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First example of a 1,3-dipolar cycloaddition of 1,3-thiazole5(4H)-thiones with an azomethine ylide; crystal structures of a pair of stereoisomeric adducts


Mloston, Grzegorz; Linden, Anthony; Heimgartner, Heinz (1997). First example of a 1,3-dipolar cycloaddition of 1,3-thiazole5(4H)-thiones with an azomethine ylide; crystal structures of a pair of stereoisomeric adducts. Polish Journal of Chemistry, 71:32-39.

Abstract

An azomethine ylide, generated in situ by thermal ring opening of cis-1-methyl-2,3-diphenylaziridine (3), undergoes a smooth cycloaddition onto the C=S bond of 1,3-thiazole-5(4H)-thiones 1 to give the stereoisomeric spiro-thiazolidines 4 and 5. The trans-configuration of the phenyl substituents in both adducts was established by X-ray crystallography.

Abstract

An azomethine ylide, generated in situ by thermal ring opening of cis-1-methyl-2,3-diphenylaziridine (3), undergoes a smooth cycloaddition onto the C=S bond of 1,3-thiazole-5(4H)-thiones 1 to give the stereoisomeric spiro-thiazolidines 4 and 5. The trans-configuration of the phenyl substituents in both adducts was 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:1997
Deposited On:18 Nov 2013 10:07
Last Modified:07 Dec 2017 23:46
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish State Committee for Scientific Research (Grant No 3 TO9A 157 10), Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Swiss Federal Commission for Foreign Students (scholarship)

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