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2H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinen


Widmer, Ulrich; Gakis, Nikolas; Arnet, Bruno; Heimgartner, Heinz (1976). 2H-Pyrrole und Pyrrole aus 3-Phenyl-2H-azirinen. CHIMIA International Journal for Chemistry, 30(10):453-455.

Abstract

Vinyl-phosphonium salts [2] and phenyl-vinyl-sulfone or divinyl-sulfone 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 esters 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 2H-pyrrole 12.
Vinyl-phosphonium salts or vinyl sulfones can be considered equivalents of non-activated acetylenes which do not react with a.

Vinyl-phosphonium salts [2] and phenyl-vinyl-sulfone or divinyl-sulfone 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 esters 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 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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:October 1976
Deposited On:01 Dec 2014 16:02
Last Modified:05 Apr 2016 18:33
Publisher:Swiss Chemical Society
ISSN:0009-4293
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung

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