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A novel type of ring closure af amino-substituted thiocarbonyl ylides


Romanski, Jaroslaw; Mloston, Grzegorz; Linden, Anthony; Heimgartner, Heinz (1999). A novel type of ring closure af amino-substituted thiocarbonyl ylides. Polish Journal of Chemistry, 73:475-485.

Abstract

The reaction of 4,4-dimethyl-1,3-thiazole-5(4H)-thiones 7a-c with dimethyl 2-diazo-3-(phenylamino)butanoate (2), prepared from dimethyl fumarate and phenyl azide, in toluene at 80°C yielded mixtures of dimethyl 2-(4,5-dihydro-4,4-dimethyl-1,3-thiazol-5-ylidene)-3-(N-phenylamino)butanedioates of type 11 and four diastereoisomeric 4,4-dimethyl-9-phenyl-1,6-dithia-3,9-diazaspiro[4.4]non-2-ene-7,8-dicarboxylates of type 12. The formation of the products of type 12 is rationalized by a novel cyclization of intermediate thiocabonyl ylides 9. The structures of cis-12a, cis-12c, and trans-12c were established by X-ray crystallography.

Abstract

The reaction of 4,4-dimethyl-1,3-thiazole-5(4H)-thiones 7a-c with dimethyl 2-diazo-3-(phenylamino)butanoate (2), prepared from dimethyl fumarate and phenyl azide, in toluene at 80°C yielded mixtures of dimethyl 2-(4,5-dihydro-4,4-dimethyl-1,3-thiazol-5-ylidene)-3-(N-phenylamino)butanedioates of type 11 and four diastereoisomeric 4,4-dimethyl-9-phenyl-1,6-dithia-3,9-diazaspiro[4.4]non-2-ene-7,8-dicarboxylates of type 12. The formation of the products of type 12 is rationalized by a novel cyclization of intermediate thiocabonyl ylides 9. The structures of cis-12a, cis-12c, and trans-12c were established by X-ray crystallography.

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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:English
Date:1999
Deposited On:05 Nov 2013 16:50
Last Modified:05 Apr 2016 17:06
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish State Committee for Scientific Research, Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Dr. Helmut Legerlotz-Stiftung, Universität Zürich

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