Publication: 1,3-dipolare Cycloadditionen eines Carbonyl-ylids mit 1,3-Thiazol-5(4H)-thionen und Thioketonen
1,3-dipolare Cycloadditionen eines Carbonyl-ylids mit 1,3-Thiazol-5(4H)-thionen und Thioketonen
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Meier, K.-R., Linden, A., Mlostoń, G., & Heimgartner, H. (1997). 1,3-dipolare Cycloadditionen eines Carbonyl-ylids mit 1,3-Thiazol-5(4H)-thionen und Thioketonen. Helvetica Chimica Acta, 80, 1190–1204.
Abstract
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Abstract
In p-xylene at 150°, 3-phenyloxirane-2,2-dicarbonitrile (4b) and 2-phenyl-3-thia-1-azaspiro[4.4]non-1-ene-4-thione (1a) gave the three 1:1 adducts trans-3a, cis-3a, and 13a in 61, 21, and 3% yield, respectively (Scheme3). The stereoisomers trans-3a and cis-3a are the products of a regioselective 1,3-dipolar cycloaddition of carbonyl-ylide 2b, generated thermally by an electrocyclic ring opening of 4b (Scheme 6), and the C=S group of 1a. Surprisingly, 13a proved not to be a regioisomeric cycloadduct of 1 a and 2b, but an isomer formed
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- Mlostoń, Grzegorz
- Heimgartner, Heinz
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Meier, K.-R., Linden, A., Mlostoń, G., & Heimgartner, H. (1997). 1,3-dipolare Cycloadditionen eines Carbonyl-ylids mit 1,3-Thiazol-5(4H)-thionen und Thioketonen. Helvetica Chimica Acta, 80, 1190–1204.
