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Übergangsmetall-katalysierte Additionsreaktionen von 3-Phenyl-2H-azirinen und Acetylencarbonsäureestern


Inada, Akira; Heimgartner, Heinz (1982). Übergangsmetall-katalysierte Additionsreaktionen von 3-Phenyl-2H-azirinen und Acetylencarbonsäureestern. Helvetica Chimica Acta, 65(5):1489-1498.

Abstract

Transition Metal Catalyzed Addition Reactions of 3-Phenyl-2H-azirines and Alkyl Acetylene Carboxylates.
In the presence of molybdenum hexacarbonyl, the 3-phenyl-2H-azirines 1 and 7 react with alkyl acetylene carboxylates 2 via the cleavage of the C,N-double bond to give 2H-pyrroles 5 or pyrrole 9 (Table), whose structures were deduced from the spectra data, in particular 13C-NMR data. The 2H-pyrrole 5a was also obtained by treatment of a mixture of 1 and 2a with tungsten hexachloride. A tentative mechanism for the formation of the 2H-pyrroles is formulated.

Abstract

Transition Metal Catalyzed Addition Reactions of 3-Phenyl-2H-azirines and Alkyl Acetylene Carboxylates.
In the presence of molybdenum hexacarbonyl, the 3-phenyl-2H-azirines 1 and 7 react with alkyl acetylene carboxylates 2 via the cleavage of the C,N-double bond to give 2H-pyrroles 5 or pyrrole 9 (Table), whose structures were deduced from the spectra data, in particular 13C-NMR data. The 2H-pyrrole 5a was also obtained by treatment of a mixture of 1 and 2a with tungsten hexachloride. A tentative mechanism for the formation of the 2H-pyrroles is formulated.

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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:1982
Deposited On:24 Jul 2014 07:25
Last Modified:21 Nov 2017 17:24
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel

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