2H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinen
Vinyl-phosphonium salts [2] and phenyl-vinyl-sulfone or divinylsulfone react with benzonitril-methylides a (which are photochemically generated from 3-phenyl-2H-azirines 1 and 2) to give, via the nonisolated intermediates of type b, 2H-pyrrole 4 and the pyrrole 5, respectively. In the reaction of s...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1976-10-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9325 |
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| _version_ | 1849697970931367936 |
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| author | Ulrich Widmer Nikolas Gakis Bruno Arnet Heinz Heimgartner Hans Schmid |
| author_facet | Ulrich Widmer Nikolas Gakis Bruno Arnet Heinz Heimgartner Hans Schmid |
| author_sort | Ulrich Widmer |
| collection | DOAJ |
| description |
Vinyl-phosphonium salts [2] and phenyl-vinyl-sulfone or divinylsulfone react with benzonitril-methylides a (which are photochemically generated from 3-phenyl-2H-azirines 1 and 2) to give, via the nonisolated intermediates of type b, 2H-pyrrole 4 and the pyrrole 5, respectively. In the reaction of sulfone 11 it was shown that the addition reaction occurs with the retention of configuration of the olefin and with the same regioselectivity as observed in the cycloadditions of acrylic ester or acrylic nitrile with a [5]. In the case of 11 the primary photoproduct 13 (scheme 2) could be isolated, which on photolysis was converted to 4 by the formal elimination of p-tosylchloride. Under mild base catalysis, for instance with the azirine 1 as a base, elimination of p-toluenesulfinic acid occurs easily at room temperature to give the 2H-pyrrole 12.
Vinyl-phosphonium salts or vinyl-sulfones can be considered equivalents of non activated acetylenes which do not react with a.
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| format | Article |
| id | doaj-art-2b9fc8e5c17f4fdf93c432839a8889db |
| institution | DOAJ |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1976-10-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-2b9fc8e5c17f4fdf93c432839a8889db2025-08-20T03:19:03ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241976-10-01301010.2533/chimia.1976.4532H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinenUlrich Widmer0Nikolas Gakis1Bruno Arnet2Heinz Heimgartner3Hans Schmid4Organisch-chemisches Institut der Universität ZürichOrganisch-chemisches Institut der Universität ZürichOrganisch-chemisches Institut der Universität ZürichOrganisch-chemisches Institut der Universität ZürichOrganisch-chemisches Institut der Universität Zürich Vinyl-phosphonium salts [2] and phenyl-vinyl-sulfone or divinylsulfone react with benzonitril-methylides a (which are photochemically generated from 3-phenyl-2H-azirines 1 and 2) to give, via the nonisolated intermediates of type b, 2H-pyrrole 4 and the pyrrole 5, respectively. In the reaction of sulfone 11 it was shown that the addition reaction occurs with the retention of configuration of the olefin and with the same regioselectivity as observed in the cycloadditions of acrylic ester or acrylic nitrile with a [5]. In the case of 11 the primary photoproduct 13 (scheme 2) could be isolated, which on photolysis was converted to 4 by the formal elimination of p-tosylchloride. Under mild base catalysis, for instance with the azirine 1 as a base, elimination of p-toluenesulfinic acid occurs easily at room temperature to give the 2H-pyrrole 12. Vinyl-phosphonium salts or vinyl-sulfones can be considered equivalents of non activated acetylenes which do not react with a. https://www.chimia.ch/chimia/article/view/9325 |
| spellingShingle | Ulrich Widmer Nikolas Gakis Bruno Arnet Heinz Heimgartner Hans Schmid 2H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinen CHIMIA |
| title | 2H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinen |
| title_full | 2H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinen |
| title_fullStr | 2H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinen |
| title_full_unstemmed | 2H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinen |
| title_short | 2H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinen |
| title_sort | 2h pyrrole und pyrrole aus 3 phenyl 2h azirinen |
| url | https://www.chimia.ch/chimia/article/view/9325 |
| work_keys_str_mv | AT ulrichwidmer 2hpyrroleundpyrroleaus3phenyl2hazirinen AT nikolasgakis 2hpyrroleundpyrroleaus3phenyl2hazirinen AT brunoarnet 2hpyrroleundpyrroleaus3phenyl2hazirinen AT heinzheimgartner 2hpyrroleundpyrroleaus3phenyl2hazirinen AT hansschmid 2hpyrroleundpyrroleaus3phenyl2hazirinen |