Stereochemistry of the Carbon-Nitrogen Bond Cleavage by Chloroformate Esters
Nicotine reacts with chloroformic esters to give the chloro-carbamates resulting from the cleavage of the C2' –N1' bond. The reaction is shown to proceed with at least 96 to 98 % inversion of configuration. In the same way, (R)-(+)-N,N-dimethyl-α-phenethylamine gave (S)-(−)-α-phenethyl ch...
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| Main Authors: | , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1974-11-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9188 |
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| _version_ | 1850170535907950592 |
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| author | C. Hootelé J.P. Lenders |
| author_facet | C. Hootelé J.P. Lenders |
| author_sort | C. Hootelé |
| collection | DOAJ |
| description |
Nicotine reacts with chloroformic esters to give the chloro-carbamates resulting from the cleavage of the C2' –N1' bond. The reaction is shown to proceed with at least 96 to 98 % inversion of configuration. In the same way, (R)-(+)-N,N-dimethyl-α-phenethylamine gave (S)-(−)-α-phenethyl chloride with inversion.
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| format | Article |
| id | doaj-art-183f4fcfd9fb404b963b4bb8cb936526 |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1974-11-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-183f4fcfd9fb404b963b4bb8cb9365262025-08-20T02:20:27ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241974-11-01281110.2533/chimia.1974.665Stereochemistry of the Carbon-Nitrogen Bond Cleavage by Chloroformate EstersC. Hootelé0J.P. Lenders1Service de Chimie Organique - Faculté des Sciences - Université Libre de Bruxelles, BelgiqueService de Chimie Organique - Faculté des Sciences - Université Libre de Bruxelles, Belgique Nicotine reacts with chloroformic esters to give the chloro-carbamates resulting from the cleavage of the C2' –N1' bond. The reaction is shown to proceed with at least 96 to 98 % inversion of configuration. In the same way, (R)-(+)-N,N-dimethyl-α-phenethylamine gave (S)-(−)-α-phenethyl chloride with inversion. https://www.chimia.ch/chimia/article/view/9188 |
| spellingShingle | C. Hootelé J.P. Lenders Stereochemistry of the Carbon-Nitrogen Bond Cleavage by Chloroformate Esters CHIMIA |
| title | Stereochemistry of the Carbon-Nitrogen Bond Cleavage by Chloroformate Esters |
| title_full | Stereochemistry of the Carbon-Nitrogen Bond Cleavage by Chloroformate Esters |
| title_fullStr | Stereochemistry of the Carbon-Nitrogen Bond Cleavage by Chloroformate Esters |
| title_full_unstemmed | Stereochemistry of the Carbon-Nitrogen Bond Cleavage by Chloroformate Esters |
| title_short | Stereochemistry of the Carbon-Nitrogen Bond Cleavage by Chloroformate Esters |
| title_sort | stereochemistry of the carbon nitrogen bond cleavage by chloroformate esters |
| url | https://www.chimia.ch/chimia/article/view/9188 |
| work_keys_str_mv | AT chootele stereochemistryofthecarbonnitrogenbondcleavagebychloroformateesters AT jplenders stereochemistryofthecarbonnitrogenbondcleavagebychloroformateesters |