Publication: Trapping of a thiocarbonyl ylide with imidazolethiones, pyrimidinethione, and thioamides
Trapping of a thiocarbonyl ylide with imidazolethiones, pyrimidinethione, and thioamides
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Mlostoń, G., Gendek, T., Linden, A., & Heimgartner, H. (1999). Trapping of a thiocarbonyl ylide with imidazolethiones, pyrimidinethione, and thioamides. Helvetica Chimica Acta, 82, 290–296. https://doi.org/10.1002/(SICI)1522-2675(19990210)82:2<290::AID-HLCA290>3.0.CO;2-P
Abstract
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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 in
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- Mlostoń, Grzegorz
- Gendek, Tomasz
- Heimgartner, Heinz
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Mlostoń, G., Gendek, T., Linden, A., & Heimgartner, H. (1999). Trapping of a thiocarbonyl ylide with imidazolethiones, pyrimidinethione, and thioamides. Helvetica Chimica Acta, 82, 290–296. https://doi.org/10.1002/(SICI)1522-2675(19990210)82:2<290::AID-HLCA290>3.0.CO;2-P
