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List of countries by number of military and paramilitary personnel
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Countries by number of active soldiers (2009)
This is a list of countries by number of military and paramilitary personnel. It includes any government-sponsored soldiers used to further the domestic and foreign policies of their respective government. The term "country" is used in its most common use, in the sense of state which exercises sovereignty or has limited recognition.
Contents
[hide]
1 Guide to the list
2 List
3 See also
4 Notes
5 References
6 Bibliography
7 Further reading
Guide to the list
The list consists of columns which can be sorted by clicking on the appropriate title:
The names of the states, accompanied by their respective national flags.
The number of military personnel on active duty that are currently serving full-time in their military capacity.
The number of military personnel in the reserve forces that are not normally kept under arms, whose role is to be available to mobilize when necessary.
The number of personnel in paramilitary forces, armed units that are not considered part of a nation's formal military forces.
The total number of military and paramilitary personnel, and the ratio per thousand inhabitants.
As military forces around the world are constantly changing in size, no definitive list can ever be compiled.
Many of the 171 countries listed here, especially those with the highest number of total soldiers, such as the two Koreas and Vietnam, include a large number of paramilitaries, civilians and policemen in their reserve personnel. Some countries, such as Italy and Japan, have only volunteers in their armed forces; while others, such as Mauritius and Panama, have no national armies, but only a paramilitary force.
List
The following list is sourced from the 2017 edition of "The Military Balance" published annually by the International Institute for Strategic Studies.
Flag
Country
Active military
Reserve military
Paramilitary
Total
Per 1000 capita
(total)
Per 1000 capita
(active)
Afghanistan[1] 171,200 0 148,200 319,400 9.6 5.1
Albania[2] 8,000 0 500 8,500 2.8 2.6
Algeria[3] 130,000 150,000 187,200 467,200 11.6 3.2
Angola[4] 107,000 0 10,000 117,000 5.8 5.3
Antigua and Barbuda[5] 180 80 0 260 2.8 1.9
Argentina[6] 74,200 0 31,250 105,450 2.4 1.7
Armenia[7][Note 1][Note 2] 44,800 210,000 4,300 259,100 84.9 14.7
Australia[8] 57,800 21,100 0 78,900 3.4 2.5
Austria[9] 21,350 146,000 0 167,350 19.2 2.5
Azerbaijan[10] 66,950 300,000 15,000 381,950 38.7 6.8
Bahamas[11] 1,300 0 0 1,300 4 4
Bahrain[12] 8,200 0 11,260 19,460 14.1 5.9
Bangladesh[13] 157,050 0 63,900 220,950 1.4 1
Barbados[14] 610 430 0 1,040 3.6 2.1
Belarus[15] 48,000 289,500 110,000 447,500 46.8 5
Belgium[16] 29,600 6,750 0 36,350 3.2 2.6
Belize[17] 1,500 700 0 2,200 6.2 4.2
Benin[18] 7,250 0 2,500 9,750 0.9 0.7
Bolivia[19] 34,100 0 37,100 71,200 6.5 3.1
Bosnia and Herzegovina[20] 10,500 0 0 10,500 2.7 2.7
Botswana[21] 9,000 0 0 9,000 4.1 4.1
Brazil[22] 334,500 1,340,000 395,000 2,069,500 10.1 1.6
Brunei[23] 7,000 700 2,250 9,950 22.8 16
Bulgaria[24] 31,300 3,000 16,000 50,300 7 4.4
Burkina Faso[25] 11,200 0 250 11,450 0.6 0.6
Burundi[26] 30,000 0 21,000 51,000 4.6 2.7
Cambodia[27] 124,300 0 67,000 191,300 12 7.8
Cameroon[28] 14,400 0 9,000 23,400 1 0.6
Canada[29] 63,000 30,000 4,500 97,500 2.8 1.8
Cape Verde[30] 1,200 0 0 1,200 2.2 2.2
Central African Republic[31] 7,150 0 1,000 8,150 1.5 1.3
Chad[32] 30,350 0 9,500 39,850 3.4 2.6
Chile[33] 64,750 40,000 44,700 149,450 8.5 3.7
China[34] 2,183,000 510,000 660,000 3,353,000 2.4 1.6
Colombia[35] 293,200 34,950 187,900 516,050 10.9 6.2
Costa Rica[36] 0 0 9,800 9,800 2 0
Côte d'Ivoire[37] 25,400 0 0 25,400 1.1 1.1
Croatia[38] 15,550 0 3,000 18,550 4.3 3.6
Cuba[39][Note 3] 49,000 1,159,000 26,500 1,234,500 110.4 4.4
Cyprus[40] 12,000 50,000 750 62,750 52 10
Czech Republic[41] 21,950 0 3,100 25,050 2.3 2.1
Democratic Republic of the Congo[42] 134,250 0 0 134,250 1.7 1.7
Denmark[43] 16,600 45,700 0 62,300 11.1 3
Djibouti[44] 10,450 0 2,500 12,950 15.3 12.3
Dominican Republic[45] 56,050 0 15,000 71,050 6.7 5.3
Ecuador[46] 40,250 118,000 500 158,750 9.9 2.5
Egypt[47] 438,500 479,000 397,000 1,314,500 13.9 4.6
El Salvador[48] 24,500 9,900 17,000 51,400 8.3 4
Equatorial Guinea[49] 1,450 0 0 1,450 1.9 1.9
Eritrea[50] 201,750 120,000 0 321,750 54.8 34.4
Estonia[51] 6,400 12,000 15,800 34,200 27.2 5.1
Ethiopia[52] 138,000 0 0 138,000 1.3 1.3
Fiji[53] 3,500 6,000 0 9,500 10.4 3.8
Finland[54][55] 22,200 900,000 2,700 924,900 168.2 4
France[56] 202,950 68,100 103,400 374,450 5.6 3
Gabon[57] 4,700 0 2,000 6,700 3.9 2.7
Gambia[58] 800 0 0 800 0.4 0.4
Georgia[59] 20,650 0 5,400 26,050 5.3 4.2
Germany[60] 176,800 27,600 500 204,900 2.5 2.2
Ghana[61] 15,500 0 0 15,500 0.6 0.6
Greece[62] 142,950 220,500 4,000 367,450 34.1 13.3
Guatemala[63] 18,050 63,850 25,000 106,900 7 1.2
Guinea[64] 9,700 0 2,600 12,300 1 0.8
Guinea-Bissau[65] 4,450 0 0 4,450 2.5 2.5
Guyana[66] 3,400 670 0 4,070 5.5 4.6
Haiti[67] 70 0 50 120 0 0
Honduras[68] 10,700 60,000 8,000 78,700 8.8 1.2
Hungary[69] 26,500 44,000 12,000 82,500 8.4 2.7
Iceland[70] 0 0 250 250 0.7 0
India[71] 1,395,100 2,142,800 1,403,700 4,941,600 3.9 1.1
Indonesia[72] 395,500 400,000 280,000 1,075,500 4.2 1.5
Iran[73][Note 4] 523,000 350,000 40,000 913,000 11 6.3
Iraq[74] 64,000 0 145,000 209,000 5.5 1.7
Ireland[75] 9,100 2,630 0 11,730 2.4 1.8
Israel[76] 176,500 465,000 8,000 649,500 79.5 21.6
Italy[77][Note 5] 174,500 18,300 182,350 375,150 6.1 2.8
Jamaica[78] 3,450 980 0 4,430 1.5 1.2
Japan[79] 247,150 56,000 12,650 315,800 2.5 2
Jordan[80] 100,500 65,000 15,000 180,500 22.1 12.3
Kazakhstan[81] 39,000 0 31,500 70,500 3.8 2.1
Kenya[82] 24,100 0 5,000 29,100 0.6 0.5
Kosovo[83] 2,500 800 0 3,300 1.8 1.3
Kuwait[84] 15,500 23,700 7,100 46,300 16.3 5.5
Kyrgyzstan[85] 10,900 0 9,500 20,400 3.6 1.9
Laos[86] 29,100 0 100,000 129,100 18.4 4.1
Latvia[87] 5,310 7,850 0 13,160 6.7 2.7
Lebanon[88] 60,000 0 20,000 80,000 12.8 9.6
Lesotho[89] 2,000 0 0 2,000 1 1
Liberia[90] 2,050 0 0 2,050 0.5 0.5
Libya[91][Note 6] 0 0 0 0 0 0
Lithuania[92] 17,030 6,700 11,300 35,030 12.3 6
Luxembourg[93] 900 0 600 1,500 2.6 1.5
Madagascar[94] 13,500 0 8,100 21,600 0.9 0.6
Malawi[95] 5,300 0 1,500 6,800 0.4 0.3
Malaysia[96][Note 7] 109,000 51,600 269,300 429,900 13.9 3.5
Mali[97] 8,000 0 7,800 15,800 0.9 0.5
Malta[98] 1,950 180 0 2,130 5.1 4.7
Mauritania[99] 15,850 0 5,000 20,850 5.7 4.3
Mauritius[100] 0 0 2,550 2,550 1.9 0
Mexico[101] 277,150 81,500 58,900 417,550 3.4 2.3
Moldova[102] 5,150 58,000 2,400 65,550 18.7 1.5
Mongolia[103] 9,700 137,000 7,500 154,200 50.9 3.2
Montenegro[104] 1,950 0 10,100 12,050 18.7 3
Morocco[105] 195,800 150,000 50,000 395,800 11.8 5.8
Mozambique[106] 11,200 0 0 11,200 0.4 0.4
Myanmar[107] 406,000 0 107,250 513,250 9 7.1
Namibia[108] 9,900 0 6,000 15,900 6.8 4.2
Nepal[109] 96,600 0 62,000 158,600 5.5 3.3
Netherlands[110] 35,410 4,500 6,060 45,970 2.7 2.1
New Zealand[111] 8,950 2,200 0 11,150 2.5 2
Nicaragua[112] 12,000 0 0 12,000 2 2
Niger[113] 5,300 0 5,400 10,700 0.6 0.3
Nigeria[114] 118,000 0 82,000 200,000 1.1 0.6
North Korea[115][Note 8] 1,190,000 6,300,000 189,000 7,679,000 305.7 47.4
Norway[116] 24,950 45,590 0 70,540 13.4 4.7
Oman[117] 42,600 0 4,400 47,000 14 12.7
Pakistan[118] 653,800 0 282,000 935,800 4.6 3.2
Palestine[119][Note 9] 0 0
Panama[120] 0 0 22,050 22,050 6 0
Papua New Guinea[121] 1,900 0 0 1,900 0.3 0.3
Paraguay[122] 10,650 164,500 14,800 189,950 27.7 1.6
Peru[123] 81,000 188,000 77,000 346,000 11.3 2.6
Philippines[124] 125,000 131,000 90,500 346,500 3.4 1.2
Poland[125] 99,300 0 73,400 172,700 4.5 2.6
Portugal[126] 29,600 211,950 44,000 285,550 26.4 2.7
Qatar[127] 11,800 0 0 11,800 5.2 5.2
Republic of Macedonia[128] 8,000 4,850 0 12,850 6.1 3.8
Republic of the Congo[129] 10,000 0 2,000 12,000 2.5 2.1
Romania[130] 70,500 50,000 79,900 200,400 9.3 3.3
Russia[131][Note 10] 831,000 2,000,000 659,000 3,490,000 24.5 5.8
Rwanda[132] 33,000 0 2,000 35,000 2.7 2.5
Saudi Arabia[133] 227,000 0 24,500 251,500 8.9 8.1
Senegal[134] 13,600 0 5,000 18,600 1.3 0.9
Serbia[135] 28,150 50,150 0 78,300 11 3.9
Seychelles[136] 420 0 0 420 4.5 4.5
Sierra Leone[137] 8,500 0 0 8,500 1.4 1.4
Singapore[138] 72,500 312,500 119,100 504,100 87.2 12.5
Slovakia[139] 15,850 0 0 15,850 2.9 2.9
Slovenia[140] 7,250 1,760 5,950 14,960 7.6 3.7
Somalia[141] 19,800 0 0 19,800 1.8 1.8
South Africa[142] 67,100 15,050 0 82,150 1.5 1.2
South Korea[143] 630,000 7,500,000 4,500 8,134,500 159.7 12.4
Spain[144] 123,200 8,200 76,750 208,150 4.3 2.5
Sri Lanka[145] 243,000 35,900 62,200 341,100 15.3 10.9
South Sudan[146] 185,000 0 0 185,000 14.8 14.8
Sudan[147] 244,300 85,000 20,000 349,300 9.5 6.7
Suriname[148] 1,840 0 100 1,940 3.3 3.1
Sweden[149] 29,750 0 21,950 51,700 5.2 3
Switzerland[150] 20,950 144,270 74,000 239,220 29.2 2.6
Syria[151] 127,500 0 150,000 277,500 16.1 7.4
Taiwan[152] 215,000 1,657,000 17,000 1,889,000 80.5 9.2
Tajikistan[153] 8,800 0 7,500 16,300 2 1.1
Tanzania[154] 27,000 80,000 1,400 108,400 2.1 0.5
Thailand[155] 360,850 245,000 93,700 699,550 10.3 5.3
Timor Leste[156] 1,330 0 0 1,330 1.1 1.1
Togo[157] 8,550 0 750 9,300 1.2 1.1
Trinidad and Tobago[158] 4,050 0 0 4,050 3.3 3.3
Tunisia[159] 35,800 0 12,000 47,800 4.3 3.2
Turkey[160] 355,200 378,700 156,800 890,700 11.1 4.4
Turkmenistan[161] 36,500 0 0 36,500 6.9 6.9
Uganda[162] 45,000 10,000 1,400 56,400 1.5 1.2
Ukraine[163] 204,000 900,000 88,000 1,192,000 27 4.6
United Arab Emirates[164] 63,000 0 0 63,000 10.6 10.6
United Kingdom[165] 152,350 81,350 0 233,700 3.6 2.4
United States[166] 1,347,300 865,050 14,850 2,227,200 6.9 4.2
Uruguay[167] 24,650 0 800 25,450 7.6 7.4
Uzbekistan[168] 48,000 0 20,000 68,000 2.3 1.6
Venezuela[169] 115,000 8,000 0 123,000 4 3.7
Vietnam[170] 482,000 5,000,000 40,000 5,522,000 58 5.1
Yemen[171] 20,000 0 0 20,000 0.7 0.7
Zambia[172] 15,100 3,000 1,400 19,500 1.3 1
Zimbabwe[173] 29,000 0 21,800 50,800 3.5 2
Not included in the list are the militaries of Abkhazia, Andorra, Bhutan, Northern Cyprus, Maldives, Monaco, Nagorno-Karabakh, San Marino, Saint Kitts and Nevis, São Tomé and Príncipe, Somaliland, Swaziland, Tonga and Vanuatu.
See also
List of countries by level of military equipment
List of countries by military expenditures
List of countries by military expenditure per capita
List of countries by Military Strength Index
List of countries by Global Militarization Index
List of countries without armed forces
List of militaries by country
List of militaries that recruit foreigners
List of countries by number of police officers
Notes
Jump up ^ The reserve military of Armenia consists mostly of ex-conscripts who have seen service within the last 15 years.
Jump up ^ Does not include Army forces of Nagorno Karabakh, which has an Armenian backed army.
Jump up ^ The reserve paramilitary of Cuba consists of the Youth Labour Army, Civil Defence and Territorial Troops Militia and count 1,120,000 units. Ready reserves serve 45 days per year.
Jump up ^ The paramilitary forces of Iran largely consists of the Basij, a paramilitary militia with claimed membership of 12.6 million (including women and children), which after mobilization can reach about 1,000,000 people able to fight.
Jump up ^ The paramilitary forces of Italy consists of the Carabinieri and the Guardia di Finanza.
Jump up ^ No data due to the ongoing civil war.
Jump up ^ The paramilitary forces of Malaysia includes 244,700 personnel from the People's Volunteer Corps.
Jump up ^ The Worker-Peasant Red Guards count 5,700,000 units and are used as a reserve paramilitary.
Jump up ^ Precise personnel-strength figures for the various Palestinian groups are not known.
Jump up ^ The potential reserve personnel of Russia may be as high as 20 million, depending on how the figures are counted. However, an est. 2 million have seen military service within the last 5 years.
References
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Bibliography
International Institute for Strategic Studies (3 February 2010). The Military Balance 2010. London: Routledge. ISBN 1857435575.
International Institute for Strategic Studies (2 March 2011). The Military Balance 2011. London: Routledge. ISBN 1857436067.
International Institute for Strategic Studies (7 March 2012). The Military Balance 2012. London: Routledge. ISBN 1857436423.
International Institute for Strategic Studies (14 March 2013). The Military Balance 2013. London: Routledge. ISBN 1857436806.
International Institute for Strategic Studies (3 February 2014). The Military Balance 2014. London: Routledge. ISBN 9781857437225.
Further reading
Cordesman, Anthony; Fitzgerald, Erin (27 August 2009). The 2010 Quadriennal Defense Review (PDF). Center for Strategic and International Studies. Retrieved 31 August 2010.
Cordesman, Anthony; Nerguizian, Aram (22 April 2010). The Gulf Military Balance in 2010 (PDF). Center for Strategic and International Studies. Retrieved 31 August 2010.
Cordesman, Anthony; Nerguizian, Aram (29 June 2010). The Arab-Israeli Military Balance (PDF). Center for Strategic and International Studies. ISBN 0275969398. Retrieved 31 August 2010.
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Freedom of the City
From Wikipedia, the free encyclopedia
Jump to: navigation, search
For the Northern Irish play, see The Freedom of the City. For the role-playing game campaign setting, see Freedom City.
"Key to the City" redirects here. For other meanings of the term, see Key to the City (disambiguation).
Award to Robert Hadfield by the City of Sheffield
Gold New York City 'Freedom of the City Box' presented to Commodore Daniel Patterson, made by Jonathan Wilmarth, John L. Moffat, and Joseph Curtis, 1832
"Ferdinand Receives the Keys of the City from the Virgin of Ghent", print after a painting made by Antoon van den Heuvel for the Joyous Entry by the Cardinal-Infante Ferdinand into Ghent in 1635
The Freedom of the City is an honour bestowed by a municipality upon a valued member of the community, or upon a visiting celebrity or dignitary. Arising from the medieval practice of granting respected citizens freedom from serfdom, the tradition still lives on in countries such as the United Kingdom, Ireland, Australia, Canada, South Africa and New Zealand – although today the title of "freeman" confers no special privileges. The Freedom of the City can also be granted by municipal authorities to military units which have earned the city's trust; in this context, it is sometimes called the Freedom of Entry. This allows them the freedom to parade through the city, and is an affirmation of the bond between the regiment and the citizenry.
The honour was sometimes accompanied by a "freedom box", a small gold box inscribed to record the occasion; these are not usual today. In some countries, such as the United States, esteemed residents and visitors may instead be presented with the Key to the City, a similarly symbolic honour. Other US cities award Honorary Citizenship, with just a certificate.
Contents
[hide]
1 Military privilege
2 Entitlement to civil privileges
2.1 United Kingdom
2.1.1 Freedom of the City of London
2.1.2 Freedom of the City of York
2.2 Ireland
3 Key to the city
4 See also
5 References
6 External links
Military privilege[edit]
Members of No. 28 Squadron RAAF marching through the centre of Canberra during the unit's Freedom of the City parade in August 2013
Freedom of the City is an ancient honour granted to martial organisations, allowing them the privilege to march into the city "with drums beating, colours flying, and bayonets fixed".[1]
This honour dates back to ancient Rome which regarded the "pomerium", the boundary of the city, as sacred. Promagistrates and generals were forbidden from entering it, and resigned their imperium immediately upon crossing it. An exception was made for victory celebrations (called triumphs), during which the victorious general would be permitted to enter for one day only. Under the Republic, soldiers also lost their status when entering, becoming citizens: thus soldiers at their general's triumph wore civilian dress. Weapons were also banned inside the pomerium for religious and traditional reasons. (The assassination of Julius Caesar occurred outside this boundary.)
Similar laws were passed by other European cities throughout the Medieval era, to protect public security and civic rights, even against their own king's troops. As a result, soldiers would be forced to camp outside the walls of the city during the winter months. The Freedom of the City was an honour granted only to troops which had earned the trust of the local populace, either through some valiant action or simply by being a familiar presence.[1]
Today, martial freedom of the city is an entirely ceremonial honour, usually bestowed upon a unit with historic ties to the area, as a token of appreciation for their long and dedicated service. The awarding of the Freedom is often accompanied by a celebratory parade through the city.
Entitlement to civil privileges[edit]
A slightly more common freedom of the city is connected to the medieval concept of "free status", when city and town charters drew a distinction between freemen and vassals of a feudal lord. As such, freemen actually pre-date 'boroughs'. Early freedom of the boroughs ceremonies had great importance in affirming that the recipient enjoyed privileges such as the right to trade and own property, and protection within the town.
In modern society, the award of honorary freedom of the city or borough tends to be entirely ceremonial, given by the local government in many towns and cities on those who have served in some exceptional capacity, or upon any whom the city wishes to bestow an honour.
United Kingdom[edit]
A recipient of Freedom of the City of London, Nigel Cumberland, after his ceremony
Before parliamentary reform in 1832, freedom of the city or town conferred the right to vote in the 'parliamentary boroughs' for the MPs. Until the Municipal Corporations Act 1835 the freemen were the exclusive electorate for some of the boroughs. These two acts together curtailed the power of the freemen and extended the franchise to all 'householders' (defined as local rate payers; in fact therefore property owners). The private property belonging to the freemen collectively was retained. The freemen of York, Oxford and Newcastle upon Tyne still own considerable areas within their towns, although the income is effectively given to support charitable objects. The Local Government Act 1972 specifically preserved freemen's rights.[2] The Local Democracy, Economic Development and Construction Act 2009 removed any restrictions entitling only men to be freemen.[3]
Today, the grant of honorary freedom in the United Kingdom is governed by the Local Government Act 1972 (as amended by the Local Democracy, Economic Development and Construction Act 2009). The 1972 Act enabled the councils of cities, royal boroughs, boroughs, and parishes (or, in Wales, communities) with the status of a royal town to confer the status of honorary freeman on "persons of distinction and persons who have, in the opinion of the council, rendered eminent services" to the local area.[4] The 2009 Act extends the ability to grant the status of honorary freeman to any county, city, district, borough, town, parish or community council (so removing the requirement for the town to have 'royal' status, and also enabling county councils to confer the honour).[5] A special meeting of the council can grant the honour by passing a resolution with a two-thirds majority at a specially convened meeting.
The exact qualifications for borough freedom differ between each city or town, but generally fall into two categories, 'patrimony' (inheritance) and 'servitude' (apprenticeship). For example, in Chester, only the children or grandchildren of freemen may apply for admission. In York, this extends to great- and great-great-grandchildren, and apprenticeship to a freeman of the city will also allow admission.[6] In Great Grimsby, the widow of a freeman passes his rights to her second husband, who retains the privilege after either divorce from or death of the widow. The borough freedom is strongest in York, Chester, Newcastle upon Tyne and Coventry; in Coventry, freedom is qualified by having served an apprenticeship. Durham and Northampton have extended their admission criteria to those who have served an apprenticeship without being 'bound' (trained) by a freeman directly. Freemen of Newcastle upon Tyne are bestowed the right to graze cattle on the town moor.[7]
Freedom of the City of London[edit]
Lord Nelson's certificate given him after becoming a Freeman of the City of London showing that he has Freedom
Ari Norman's Certificate of Freedom of the City of London
Sir Tim Berners-Lee receiving the freedom of the City of London in 2014
In England, the most established borough freedom is that conferred by the Freedom of the City of London, first recorded in 1237. This is closely tied to the role and status of the livery companies. From 1835, the freedom "without the intervention of a Livery Company" has been bestowed by a general resolution of Common Council, by "redemption" (purchase), at one time for an onerous sum, but now for a donation to the Freemen's School.[8]
New freemen are enrolled in a ceremony in Guildhall, when they receive a guide to conducting their lives in an honourable fashion and an impressive sealed certificate. Freemen's children get admission preference at the City of London Freemen's School. There are a number of rights traditionally but apocryphally associated with freemen—the right to drive sheep and cattle over London Bridge; to a silken rope, if hanged; to carry a naked sword in public; or that if the City of London Police finds a freeman drunk and incapable, they will bundle him or her into a taxi and send them home rather than throw them into a cell. While sheep have occasionally been driven over London Bridge on special occasions, the rest of these "privileges" are now effectively symbolic.
Mark Stephens with a sheep on London Bridge in 2009
The right to herd sheep and cattle across London's four bridges technically no longer applies, as there are no livestock markets in the city.[9] Nevertheless, this right has been exercised, or the city has granted permission, periodically in modern times:
On 19 August 1999, Jef Smith, a freeman of London walked two sheep over Tower Bridge to bring attention to the rights of older citizens.[9]
On 17 June 2006, a flock of about thirty sheep was driven across the Millennium Bridge to mark the start of London Architecture Week.[10]
On 31 August 2008, Amanda Cottrell, former High Sheriff of Kent, marched six rams across London Bridge to promote fundraising for the restoration of Canterbury Cathedral and "a scheme backing local food production".[11]
On 17 September 2008, the Lord Mayor of London, David Lewis, and some 500 freemen drove a flock of Romney ewes in relay across London Bridge to raise funds for the Lord Mayor's charities (Orbis and Wellbeing of Women).[12]
Freedom of the City of York[edit]
York has a long history of freemen dating back to the Anglo-Saxon period, with records dating back to 1272.[13] Freemen may claim their rights through patronage (as far back as their great-great-grandparent, there are records of women being admitted in York in medieval times, a right forgotten for a time until the late 1970's when the Gild carried out research and rediscovered it) or apprenticeship. Once 'sworn in', freemen can join the Gild (Archaic spelling used) of Freemen who continue to take an interest in the affairs of the city. New admissions are made every year (usually October) following an admission ceremony with the Lord Mayor at the Guildhall.
Ireland[edit]
This section is about Ireland. For Freedom awarded specifically in Dublin, see Freedom of the City of Dublin.
In Ireland, borough freedom of the city is generally given to noted foreign and national dignitaries and the list rarely exceeds a few dozen. As in the United Kingdom, the title generally comes with various ancient privileges – for instance, freemen of Dublin are allowed the right to vote in certain elections, bring goods for sale in the city without customs and the right to pasture sheep on common ground such as College Green and St. Stephen's Green.
Key to the city[edit]
Russian President Dmitry Medvedev received the Golden Key to the City of Madrid during his state visit to Spain in March 2009.
See also: List of Keys to the City in the United States and List of Keys to the City in Canada
For other uses, see Key to the City (disambiguation).
In some countries, such as the United States, an ornamental key – the "Key to the City" – is presented to esteemed visitors, residents, or others whom the city wishes to honour. This practice is a variation on the Freedom of the City tradition, and has a similar symbolic meaning; evoking medieval walled cities, the gates of which would be guarded during the day and locked at night, the key symbolises the freedom of the recipient to enter and leave the city at will, as a trusted friend of city residents.[14]
In some cities in the Netherlands, Belgium, and Germany, the key to the city is given to the so-called "prince carnival (nl)" who leads the carnivals which take place the week prior to Septuagesima. The tradition is that the mayor steps down for this period and power is transferred to the prince carnival, who then returns the key at the end of Shrove Tuesday/Mardi Gras. Today, the handing over of the key is mostly symbolic and marks the start and end of the carnival.
In Calgary, Alberta, Canada, instead of a key, esteemed visitors receive a white cowboy hat and usually recite one of two oaths (one formal, the other more silly) to become honorary Calgarians.[15]
See also[edit]
List of Freedom of the City recipients (military)
Honorary citizenship
References[edit]
^ Jump up to: a b "1985 – 75th Anniversary Naval Service of Canada". Royal Canadian Navy. Archived from the original on 12 September 2012. Retrieved 21 November 2012.
Jump up ^ Section 248 of Text of the Local Government Act 1972 as in force today (including any amendments) within the United Kingdom, from legislation.gov.uk
Jump up ^ Sections 27 and 28 of the Text of the Local Democracy, Economic Development and Construction Act 2009 as in force today (including any amendments) within the United Kingdom, from legislation.gov.uk
Jump up ^ Text of the Section 249 of the Local Government Act 1972 as in force today (including any amendments) within the United Kingdom, from legislation.gov.uk
Jump up ^ Text of the Section 249 of the Local Democracy, Economic Development and Construction Act 2009 as in force today (including any amendments) within the United Kingdom, from legislation.gov.uk
Jump up ^ "The Gild of Freemen of the City of York". Retrieved 24 June 2011.
Jump up ^ "The Moor". The Freemen of Newcastle upon Tyne. Archived from the original on 8 October 2013. Retrieved 13 November 2013.
Jump up ^ "Freedom of the City". City of London. Archived from the original on 13 January 2016.
^ Jump up to: a b "Protest Freeman herds sheep over Tower Bridge". BBC News. 19 August 1999. Retrieved 15 November 2010.
Jump up ^ "Sheep flock driven through city". BBC News. 17 June 2006. Retrieved 4 January 2010.
Jump up ^ "Sheep marched over London Bridge". BBC News. 31 August 2008. Retrieved 4 January 2010.
Jump up ^ "Sheep march over bridge for money". BBC News. 19 September 2008. Retrieved 4 January 2010.
Jump up ^ "Register of the Freemen of the City of York - British History Online". www.british-history.ac.uk.
Jump up ^ "Key to the City of New York". New York City Commission for the United Nations, Consular Corps and Protocol. Archived from the original on 14 November 2011. Retrieved 6 November 2011.
Jump up ^ "White Hat Ceremony". Visit Calgary. Archived from the original on 22 November 2012.
External links[edit]
Guild of Freemen of the City of London
Freedom of the City of London
The Gild of Freemen of the City of York
Freemen of the City of Liverpool
Retrieved from "https://en.wikipedia.org/w/index.php?title=Freedom_of_the_City&oldid=837920831"
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Wittig reaction
From Wikipedia, the free encyclopedia
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Wittig reaction
Named after Georg Wittig
Reaction type Coupling reaction
Reaction
aldehyde or ketone
+
triphenyl phosphonium ylide
↓
alkene
+
triphenylphosphine oxide
Conditions
Typical solvents typically THF or diethyl ether
Identifiers
March's Advanced Organic Chemistry 16–44 (6th ed.)
Organic Chemistry Portal wittig-reaction
RSC ontology ID RXNO:0000015 Y
N(what is this?) (verify)
The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide (often called a Wittig reagent) to give an alkene and triphenylphosphine oxide.[1][2]
The Wittig reaction was discovered in 1954 by Georg Wittig, for which he was awarded the Nobel Prize in Chemistry in 1979. It is widely used in organic synthesis for the preparation of alkenes.[3][4][5] It should not be confused with the Wittig rearrangement.
Wittig reactions are most commonly used to couple aldehydes and ketones to singly substituted phosphine ylides. With unstabilised ylides this results in almost exclusively the Z-alkene product. In order to obtain the E-alkene, stabilised ylides are used in the Horner–Wadsworth–Emmons reaction or unstabilised ylides are used in the Schlosser modification of the Wittig reaction.
Contents
[hide]
1 Reaction mechanism
1.1 Classical mechanism
1.2 Mechanism
2 Wittig reagents
2.1 Preparation of phosphorus ylides
2.2 Structure of the ylide
2.3 Reactivity
3 Scope and limitations
3.1 Schlosser modification
4 Examples
5 See also
6 References
7 External links
Reaction mechanism[edit]
Classical mechanism[edit]
The steric bulk of the ylide 1 influences the stereochemical outcome of nucleophilic addition to give a predominance of the betaine 3 (cf. Bürgi–Dunitz angle). Note that for betaine 3 both R1 and R2 as well as PPh3+ and O− are positioned anti to one another.
Carbon-carbon bond rotation gives the betaine 4, which then forms the oxaphosphetane 5. Elimination gives the desired Z-alkene 7 and triphenylphosphine oxide 6. With simple Wittig reagents, the first step occurs easily with both aldehydes and ketones, and the decomposition of the betaine (to form 5) is the rate-determining step. However, with stabilised ylides (where R1 stabilises the negative charge) the first step is the slowest step, so the overall rate of alkene formation decreases and a bigger proportion of the alkene product is the E-isomer. This also explains why stabilised reagents fail to react well with sterically hindered ketones.
Mechanism[edit]
Mechanistic studies have focused on unstabilized ylides, because the intermediates can be followed by NMR spectroscopy. The existence and interconversion of the betaine (3a and 3b) is subject of ongoing research.[6] Phosphonium ylides 1 react with carbonyl compounds 2 via a π²s/π²a [2+2] cycloaddition to directly form the oxaphosphetanes 4a and 4b. The stereochemistry of the product 5 is due to the addition of the ylide 1 to the carbonyl 2 and to the equilibration of the intermediates.[7][8][9] Maryanoff and Reitz identified the issue about equilibration of Wittig intermediates and termed the process "stereochemical drift". For many years, the stereochemistry of the Wittig reaction, in terms of carbon-carbon bond formation, had been assumed to correspond directly with the Z/E stereochemistry of the alkene products. However, certain reactants do not follow this simple pattern. Lithium salts can also exert a profound effect on the stereochemical outcome.[10]
Mechanisms differ for aliphatic and aromatic aldehydes and for aromatic and aliphatic phosphonium ylides. Evidence suggests that the Wittig reaction of unbranched aldehydes under lithium-salt-free conditions do not equilibrate and are therefore under kinetic reaction control.[11][12] Vedejs has put forth a theory to explain the stereoselectivity of stabilized and unstabilized Wittig reactions.[13]
Wittig reagents[edit]
Preparation of phosphorus ylides[edit]
Wittig reagents are usually prepared from a phosphonium salt, which is in turn prepared by the quaternization of triphenylphosphine with an alkyl halide. The alkylphosphonium salt is deprotonated with a strong base such as n-butyllithium:
[Ph3P+CH2R]X− + C4H9Li → Ph3P=CHR + LiX + C4H10
One of the simplest ylide is methylenetriphenylphosphorane (Ph3P=CH2).[14] It is also a precursor to more elaborate Wittig reagents. Alkylation of Ph3P=CH2 with a primary alkyl halide R−CH2−X, produces substituted phosphonium salts:
Ph3P=CH2 + RCH2X → Ph3P+CH2CH2R X−
These salts can be deprotonated in the usual way to give Ph3P=CH−CH2R.
Structure of the ylide[edit]
Ball-and-stick model of Ph3P=CH2, as found in the crystal structure
The Wittig reagent may be described in the phosphorane form (the more familiar representation) or the ylide form:
The ylide form is a significant contributor, and the carbon atom is nucleophilic.
Reactivity[edit]
Simple phosphoranes are reactive. Most hydrolyze and oxidize readily. They are therefore prepared using air-free techniques. Phosphoranes are more air-stable when they contain an electron withdrawing group. Some examples are Ph3P=CHCO2R and Ph3P=CHPh. These ylides are sufficiently stable to be sold commercially [15]
From the phosphonium salts, these reagent are formed more readily, requiring only NaOH, and they are usually more air-stable.[citation needed] These are less reactive than simple ylides, and so they usually fail to react with ketones, necessitating the use of the Horner–Wadsworth–Emmons reaction as an alternative. They usually give rise to an E-alkene product when they react, rather than the more usual Z-alkene.
Scope and limitations[edit]
The Wittig reaction is a popular method for the synthesis of alkene from ketones and aldehydes. The Wittig reagent can generally tolerate carbonyl compounds containing several kinds of functional groups such as OH, OR, aromatic nitro and even ester groups[citation needed]. There can be a problem with sterically hindered ketones, where the reaction may be slow and give poor yields, particularly with stabilized ylides, and in such cases the Horner–Wadsworth–Emmons (HWE) reaction (using phosphonate esters) is preferred. Another reported limitation is the often labile nature of aldehydes which can oxidize, polymerize or decompose. In a so-called Tandem Oxidation-Wittig Process the aldehyde is formed in situ by oxidation of the corresponding alcohol.[16]
As mentioned above, the Wittig reagent itself is usually derived from a primary alkyl halide. Quaternization of triphenylphosphine with most secondary halides is inefficient. For this reason, Wittig reagents are rarely used to prepare tetrasubstituted alkenes. However the Wittig reagent can tolerate many other variants. It may contain alkenes and aromatic rings, and it is compatible with ethers and even ester groups. Even C=O and nitrile groups can be present if conjugated with the ylide- these are the stabilised ylides mentioned above. Bis-ylides (containing two P=C bonds) have also been made and used successfully.
One limitation relates to the stereochemistry of the product. With simple ylides, the product is usually mainly the Z-isomer, although a lesser amount of the E-isomer is often formed also – this is particularly true when ketones are used. If the reaction is performed in DMF in the presence of LiI or NaI, the product is almost exclusively the Z-isomer.[17] If the E-isomer is the desired product, the Schlosser modification may be used. With stabilised ylides the product is mainly the E-isomer, and this same isomer is also usual with the HWE reaction.
Schlosser modification[edit]
The major limitation of the traditional Wittig reaction is that the reaction proceeds mainly via the erythro betaine intermediate, which leads to the Z-alkene. The erythro betaine can be converted to the threo betaine using phenyllithium at low temperature.[18] This modification affords the E-alkene.
Allylic alcohols can be prepared by reaction of the betaine ylid with a second aldehyde.[19] For example:
Examples[edit]
Because of its reliability and wide applicability, the Wittig reaction has become a standard tool for synthetic organic chemists.[20]
The most popular use of the Wittig reaction is for the introduction of a methylene group using methylenetriphenylphosphorane (Ph3P=CH2). Using this reagent even a sterically hindered ketone such as camphor can be converted to its methylene derivative. In this case, the Wittig reagent is prepared in situ by deprotonation of methyltriphenylphosphonium bromide with potassium tert-butoxide.[21] In another example, the phosphorane is produced using sodium amide as a base, and this reagent converts the aldehyde shown into alkene I in 62% yield.[22] The reaction is performed in cold THF, and the sensitive nitro, azo and phenoxide groups are tolerated. The product can be used to incorporate a photostabiliser into a polymer, to protect the polymer from damage by UV radiation.
Another example of its use is in the synthesis of leukotriene A methyl ester.[23][24] The first step uses a stabilised ylide, where the carbonyl group is conjugated with the ylide preventing self condensation, although unexpectedly this gives mainly the cis product. The second Wittig reaction uses a non-stabilised Wittig reagent, and as expected this gives mainly the cis product. Note that the epoxide and ester functional groups survive intact.
Methoxymethylenetriphenylphosphine is a Wittig reagent for the homologation of aldehydes.
See also[edit]
Wikimedia Commons has media related to Wittig reaction.
Corey–Chaykovsky reagent
Horner–Wadsworth–Emmons reaction
Julia–Lythgoe olefination
Peterson olefination
Tebbe's reagent
Organophosphorus chemistry
Homologation reaction
Kauffmann olefination
Titanium-Zinc Methylenation
References[edit]
Jump up ^ Georg Wittig, Ulrich Schöllkopf (1954). "Über Triphenyl-phosphin-methylene als olefinbildende Reagenzien I". Chemische Berichte. 87 (9): 1318. doi:10.1002/cber.19540870919.
Jump up ^ Georg Wittig; Werner Haag (1955). "Über Triphenyl-phosphin-methylene als olefinbildende Reagenzien II". Chemische Berichte. 88 (11): 1654–1666. doi:10.1002/cber.19550881110.
Jump up ^ Maercker, A. Org. React. 1965, 14, 270–490. (Review)
Jump up ^ W. Carruthers, Some Modern Methods of Organic Synthesis, Cambridge University Press, Cambridge, UK, 1971, 81–90. (ISBN 0-521-31117-9)
Jump up ^ R. W. Hoffmann (2001). "Wittig and His Accomplishments: Still Relevant Beyond His 100th Birthday". Angewandte Chemie International Edition. 40 (8): 1411–1416. doi:10.1002/1521-3773(20010417)40:8<1411::AID-ANIE1411>3.0.CO;2-U. PMID 11317288.
Jump up ^ E. Vedejs & C. F. Marth (1990). "Mechanism of Wittig reaction: evidence against betaine intermediates". J. Am. Chem. Soc. 112 (10): 3905–3909. doi:10.1021/ja00166a026.
Jump up ^ B. E. Maryanoff, A. B. Reitz, M. S. Mutter, R. R. Inners, and H. R. Almond, Jr., "Detailed Rate Studies on the Wittig Reaction of Non-Stabilized Phosphorus Ylides via 31P, 1H, and 13C NMR Spectroscopy. Insight into Kinetic vs. Thermodynamic Control of Stereochemistry", J. Am. Chem. Soc., 107, 1068–1070 (1985)
Jump up ^ B. E. Maryanoff, A. B. Reitz, D. W. Graden, and H. R. Almond, Jr., "NMR Rate Study on the Wittig Reaction of 2,2-Dimethylpropanal and Tributylbutylidene-phosphorane", Tetrahedron Lett., 30, 1361–1364 (1989)
Jump up ^ B. E. Maryanoff, A. B. Reitz, M. S. Mutter, R. R. Inners, H. R. Almond, Jr., R. R. Whittle, and R. A. Olofson, "Stereochemistry and Mechanism of the Wittig Reaction. Diastereomeric Reaction Intermediates and Analysis of the Reaction Course", J. Am. Chem. Soc., 108, 7664–7678 (1986)
Jump up ^ A. B. Reitz, S. O. Nortey, A. D. Jordan, Jr., M. S. Mutter, and B. E. Maryanoff, "Dramatic Concentration Dependence of Stereochemistry in the Wittig Reaction. Examination of the Lithium-Salt Effect", J. Org. Chem., 51, 3302–3308 (1986)
Jump up ^ E. Vedejs, C. F. Marth and R. Ruggeri (1988). "Substituent effects and the Wittig mechanism: the case of stereospecific oxaphosphetane decomposition". J. Am. Chem. Soc. 110 (12): 3940–48. doi:10.1021/ja00220a036.
Jump up ^ E. Vedejs & C. F. Marth (1988). "Mechanism of the Wittig reaction: the role of substituents at phosphorus". J. Am. Chem. Soc. 110 (12): 3948–3958. doi:10.1021/ja00220a037.
Jump up ^ Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1.
Jump up ^ George Wittig U. Schoellkopf (1973). "Methylenecyclohexane (describes Ph3PCH2". Organic Syntheses. ; Collective Volume, 5, p. 751
Jump up ^ http://www.sigmaaldrich.com/catalog/product/aldrich/c5106?lang=en&region=IN
Jump up ^ Richard J. K. Taylor, Leonie Campbell, and Graeme D. McAllister (2008). "(±) trans-3,3'-(1,2-Cyclopropanediyl)bis-2-(E)-propenoic Acid, Diethyl Ester: Tandem Oxidation Procedure (TOP) using MnO2 Oxidation-Stabilized Phosphorane Trapping" (PDF). Organic Syntheses. 85: 15–26. CS1 maint: Multiple names: authors list (link)
Jump up ^ L. D. Bergelson & M. M. Shemyakin (1964). "Synthesis of Naturally Occurring Unsaturated Fatty Acids by Sterically Controlled Carbonyl Olefination". Angew. Chem. 3 (4): 250–260. doi:10.1002/anie.196402501.
Jump up ^ M. Schlosser & K. F. Christmann (1966). "Trans-Selective Olefin Syntheses". Angewandte Chemie International Edition in English. 5 (1): 126. doi:10.1002/anie.196601261.
Jump up ^ E. J. Corey and H. Yamamoto (1970). "Modification of the Wittig reaction to permit the stereospecific synthesis of certain trisubstituted olefins. Stereospecific synthesis of α-santalol". J. Am. Chem. Soc. 92 (1): 226–228. doi:10.1021/ja00704a052.
Jump up ^ B. E. Maryanoff & A. B. Reitz (1989). "The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects". Chem. Rev. 89 (4): 863–927. doi:10.1021/cr00094a007.
Jump up ^ Fitjer, L.; Quabeck, U. Synthetic Communications 1985, 15(10), 855–864.
Jump up ^ F. A. Bottino, G. Di Pasquale, A. Pollicino, A. Recca and D. T. Clark (1990). "Synthesis of 2-(2-hydroxyphenyl)-2H-benzotriazole monomers and studies of the surface photostabilization of the related copolymers". Macromolecules. 23 (10): 2662–2666. Bibcode:1990MaMol..23.2662B. doi:10.1021/ma00212a011. CS1 maint: Multiple names: authors list (link)
Jump up ^ I. Ernest, A. J. Main and R. Menasse (1982). "Synthesis of the 7-cis isomer of the natural leukotriene d4". Tetrahedron Letters. 23 (2): 167–170. doi:10.1016/S0040-4039(00)86776-3.
Jump up ^ E. J. Corey, D. A. Clark, G. Goto, A. Marfat, C. Mioskowski, B. Samuelsson and S. Hammarstroem (1980). "Stereospecific total synthesis of a "slow reacting substance" of anaphylaxis, leukotriene C-1". J. Am. Chem. Soc. 102 (4): 1436–1439. doi:10.1021/ja00524a045. CS1 maint: Multiple names: authors list (link)
External links[edit]
Wittig reaction in Organic Syntheses, Coll. Vol. 10, p. 703 (2004); Vol. 75, p. 153 (1998). (Article)
Wittig reaction in Organic Syntheses, Coll. Vol. 5, p. 361 (1973); Vol. 45, p. 33 (1965). (Article)
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