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Trapping of a thiocarbonyl ylide with imidazolethiones, pyrimidinethione, and thioamides


Mloston, Grzegorz; Gendek, Tomasz; Linden, Anthony; Heimgartner, Heinz (1999). Trapping of a thiocarbonyl ylide with imidazolethiones, pyrimidinethione, and thioamides. Helvetica Chimica Acta, 82:290-296.

Abstract

The reactions of 1,1,3,3-tetramethyl-8-thia-5,6-diazaspirol[3.4]oct-5-en-2-one (1a) with imidazole-2-thiones 3 and pyrimidine-2(1H)-thione (6) in CHCl3 at 40 - 50° yield 2,2,4,4-tetramethylcyclobutanone dithioacetals of type 4 and 7, respectively, by interception of the intermediate thiocarbonyl ylide 2a (Scheme 2). Thiirane 5 is formed as a minor product by 1,3-dipolar electrocyclization of 2a. When thioacetamide (8a) and thiobenzamide (8b) are used as trapping reagents, the primary adduct 10 undergoes a spontaneous cyclization by intramolecular nucleophilic addition of the imino group at the carbonyl group to yield bicyclic products of type 9. The structure of 9a has been established by X-ray crystallography.

Abstract

The reactions of 1,1,3,3-tetramethyl-8-thia-5,6-diazaspirol[3.4]oct-5-en-2-one (1a) with imidazole-2-thiones 3 and pyrimidine-2(1H)-thione (6) in CHCl3 at 40 - 50° yield 2,2,4,4-tetramethylcyclobutanone dithioacetals of type 4 and 7, respectively, by interception of the intermediate thiocarbonyl ylide 2a (Scheme 2). Thiirane 5 is formed as a minor product by 1,3-dipolar electrocyclization of 2a. When thioacetamide (8a) and thiobenzamide (8b) are used as trapping reagents, the primary adduct 10 undergoes a spontaneous cyclization by intramolecular nucleophilic addition of the imino group at the carbonyl group to yield bicyclic products of type 9. The structure of 9a has been 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 16:48
Last Modified:05 Apr 2016 17:06
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Polish State Committee for Scientific Research, Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/(SICI)1522-2675(19990210)82:2<290::AID-HLCA290>3.0.CO;2-P

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