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- Title
Trapping of a Thiocarbonyl Ylide with Imidazolethiones, Pyrimidinethione, and Thioamides.
- Authors
Mlostoń, Grzegorz; Gendek, Tomasz; Linden, Anthony; Heimgartner, Heinz
- 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(1 H)-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.
- Publication
Helvetica Chimica Acta, 1999, Vol 82, Issue 2, p290
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/(SICI)1522-2675(19990210)82:2<290::AID-HLCA290>3.0.CO;2-P