A new selective dichlorination of CC double bonds
A new dichlorination procedure of CC double bond was developed with hexachloroethane as chlorinating agent and RuCl 2(PPh 3) 3 as catalyst. The reaction is highly selective for CC double bond; other functional groups are unaffected by these conditions. The reaction proceeded at the existence of va...
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| Published in | Tetrahedron letters Vol. 35; no. 5; pp. 737 - 740 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
01.01.1994
Elsevier |
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| Abstract | A new dichlorination procedure of CC double bond was developed with hexachloroethane as chlorinating agent and RuCl
2(PPh
3)
3 as catalyst. The reaction is highly selective for CC double bond; other functional groups are unaffected by these conditions.
The reaction proceeded at the existence of various kinds of functional groups, such as hydoxy, carboxyl, ester phenyl, of active methylene in the structure. |
|---|---|
| AbstractList | A new dichlorination procedure of C-C double bond was developed with hexachloroethane as chlorinating agent and RuCl2(PPh(3))(3) as catalyst. The reaction is highly selective for C-C double bond; other functional groups are unaffected by these conditions. A new dichlorination procedure of CC double bond was developed with hexachloroethane as chlorinating agent and RuCl 2(PPh 3) 3 as catalyst. The reaction is highly selective for CC double bond; other functional groups are unaffected by these conditions. The reaction proceeded at the existence of various kinds of functional groups, such as hydoxy, carboxyl, ester phenyl, of active methylene in the structure. |
| Author | Kondo, Kiyosi Sugimoto, Kikuo Sakai, Kunikazu Shigeizumi, Sanae |
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| Cites_doi | 10.1351/pac198557121827 10.1021/jo00822a021 10.1021/ja00224a043 10.1055/s-1977-24301 10.1021/ja01183a053 10.1016/0022-328X(84)80210-7 10.1126/science.102.2640.128 10.1021/jo01071a005 10.1016/S0040-4020(01)97184-4 10.1016/0022-1902(66)80191-4 10.1021/jo01308a003 10.1016/0022-328X(85)88116-X |
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| Copyright | 1994 1994 INIST-CNRS |
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| Keywords | ALKENES OLEFINS MECHANISM ADDITIONS RUCL2(PPH3)3 ORGANIC POLYHALIDES Chlorination Tertiary phosphine Conjugated dienic compound Chloro complex Selectivity Ethylenic compound Ruthenium II Complexes |
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| References_xml | – volume: 28 start-page: 945 year: 1966 ident: BIB11 publication-title: J. Inorg. Nucl. Chem. contributor: fullname: Wilkinson – volume: 280 start-page: 397 year: 1985 ident: BIB13 publication-title: J. Organometal. Chem. contributor: fullname: Durrant – start-page: 1515 year: 1987 ident: BIB5 publication-title: J. Chem. Soc. contributor: fullname: Stevenson – volume: 25 start-page: 3508 year: 1971 ident: BIB10 publication-title: Bull. Chem. Soc. Chim. Fr. contributor: fullname: Kovacic – start-page: 128 year: 1972 ident: BIB7 publication-title: ACS Symposium Series No 42 contributor: fullname: Negishi – volume: 41 start-page: 4057 year: 1985 ident: BIB9 publication-title: Tetrahedron contributor: fullname: Bellus – volume: 70 start-page: 1055 year: 1948 ident: BIB2 publication-title: J. Am. Chem. Soc. contributor: fullname: Fisher – volume: 45 start-page: 3957 year: 1980 ident: BIB4 publication-title: J. Org. 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THE ADDITION OF BROMO ESTERS TO OLEFINS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: KHARASCH, MS – volume: 25 start-page: 20 year: 1960 ident: WOS:A1960WT07500005 article-title: TETRABUTYLAMMONIUM IODOTETRACHLORIDE AS A CHLORINATING AGENT publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BUCKLES, RE – start-page: 1515 year: 1987 ident: WOS:A1987J144700017 article-title: RUTHENIUM(II)-CATALYZED AND RHENIUM(III)-CATALYZED ADDITION OF TETRAHALOGENOMETHANES TO ALKENES AND 1, OMEGA-DIENES - STEREOSELECTIVE FORMATION OF CIS-1,2-DISUBSTITUTED CYCLOPENTANES FROM 1,6-DIENES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: GRIGG, R – volume: 57 start-page: 1827 year: 1985 ident: WOS:A1985AUV7700010 article-title: COPPER-CATALYZED ADDITIONS OF ORGANIC POLYHALIDES TO OLEFINS - A VERSATILE SYNTHETIC TOOL publication-title: PURE AND APPLIED CHEMISTRY contributor: fullname: BELLUS, D – volume: 110 start-page: 3957 year: 1988 ident: WOS:A1994MU47700022.9 publication-title: J AM CHEM SOC contributor: fullname: HAYES TK – volume: 280 start-page: 397 year: 1985 ident: WOS:A1985ABJ5800011 article-title: THE MECHANISM OF THE ADDITION OF HALOALKANES TO ALKENES IN THE PRESENCE OF DICHLOROTRIS(TRIPHENYLPHOSPHINE)-RUTHENIUM(II), [RUCL2(PPH3)3] publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: BLAND, WJ – start-page: 145 year: 1977 ident: WOS:A1994MU47700022.7 publication-title: SYNTHESIS-STUTTGART contributor: fullname: FRIEDLINA RK – volume: 102 start-page: 128 year: 1945 ident: WOS:A1945UA52600010 article-title: ADDITION OF CARBON TETRACHLORIDE AND CHLOROFORM TO OLEFINS publication-title: SCIENCE contributor: fullname: KHARASCH, MS – volume: 267 start-page: C45 year: 1984 ident: WOS:A1984SX37800018 article-title: THE MECHANISM OF THE ADDITION OF TETRAHALOALKANES TO ALKENES IN THE PRESENCE OF RUCL2(PPH3)3 publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: BLAND, WJ – start-page: 3508 year: 1971 ident: WOS:A1971K665700017 article-title: REACTION OF IODOBENZENE DICHLORIDE AND OF CHLORINE WITH SEVERAL DERIVATIVES OF NORBORNENE publication-title: BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE contributor: fullname: MASSON, S – volume: 57 start-page: 1827 year: 1985 ident: 10.1016/S0040-4039(00)75804-7_BIB8 publication-title: Pure & Appl. Chem. doi: 10.1351/pac198557121827 contributor: fullname: Bellus – volume: 36 start-page: 3566 year: 1971 ident: 10.1016/S0040-4039(00)75804-7_BIB10_3 publication-title: J. Org. Chem. doi: 10.1021/jo00822a021 contributor: fullname: Field – start-page: 1515 year: 1987 ident: 10.1016/S0040-4039(00)75804-7_BIB5 publication-title: J. Chem. Soc. contributor: fullname: Grigg – volume: 110 start-page: 3957 year: 1988 ident: 10.1016/S0040-4039(00)75804-7_BIB6 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00224a043 contributor: fullname: Hayes – start-page: 145 year: 1977 ident: 10.1016/S0040-4039(00)75804-7_BIB3 publication-title: Synthesis doi: 10.1055/s-1977-24301 contributor: fullname: Friedlina – start-page: 128 year: 1972 ident: 10.1016/S0040-4039(00)75804-7_BIB7 publication-title: ACS Symposium Series No 42 contributor: fullname: Kondo – volume: 70 start-page: 1055 year: 1948 ident: 10.1016/S0040-4039(00)75804-7_BIB2 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01183a053 contributor: fullname: Kharasch – volume: 267 start-page: C45 year: 1984 ident: 10.1016/S0040-4039(00)75804-7_BIB12 publication-title: J. Organometal. Chem. doi: 10.1016/0022-328X(84)80210-7 contributor: fullname: Bland – volume: 102 start-page: 128 year: 1945 ident: 10.1016/S0040-4039(00)75804-7_BIB1 publication-title: Science (Washington, D. C.) doi: 10.1126/science.102.2640.128 contributor: fullname: Kharasch – volume: 25 start-page: 20 year: 1960 ident: 10.1016/S0040-4039(00)75804-7_BIB10_2 publication-title: J. Org. Chem. doi: 10.1021/jo01071a005 contributor: fullname: Buckle – volume: 41 start-page: 4057 year: 1985 ident: 10.1016/S0040-4039(00)75804-7_BIB9 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)97184-4 contributor: fullname: Martin – volume: 28 start-page: 945 year: 1966 ident: 10.1016/S0040-4039(00)75804-7_BIB11 publication-title: J. Inorg. Nucl. Chem. doi: 10.1016/0022-1902(66)80191-4 contributor: fullname: Stephenson – start-page: 3508 year: 1971 ident: 10.1016/S0040-4039(00)75804-7_BIB10_1 publication-title: Bull. Chem. Soc. Chim. Fr. contributor: fullname: Masson – volume: 45 start-page: 3957 year: 1980 ident: 10.1016/S0040-4039(00)75804-7_BIB4 publication-title: J. Org. Chem. doi: 10.1021/jo01308a003 contributor: fullname: Elzinger – volume: 280 start-page: 397 year: 1985 ident: 10.1016/S0040-4039(00)75804-7_BIB13 publication-title: J. Organometal. Chem. doi: 10.1016/0022-328X(85)88116-X contributor: fullname: Bland |
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| Snippet | A new dichlorination procedure of CC double bond was developed with hexachloroethane as chlorinating agent and RuCl
2(PPh
3)
3 as catalyst. The reaction is... A new dichlorination procedure of C-C double bond was developed with hexachloroethane as chlorinating agent and RuCl2(PPh(3))(3) as catalyst. The reaction is... |
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| SubjectTerms | Aliphatic compounds Chemistry Chemistry, Organic Exact sciences and technology Organic chemistry Physical Sciences Preparations and properties Science & Technology |
| Title | A new selective dichlorination of CC double bonds |
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