On the Behavior of α, β-Unsaturated Thioaldehydes and Thioketones in the Diels-Alder Reaction

…, T Nakajima, RA Zingaro, JH Reibenspies…

Index: Li, Guang Ming; Niu, Shuqiang; Segi, Masahito; Tanaka, Koichiro; Nakajima, Tadashi; Zingaro, Ralph A.; Reibenspies, Joseph H.; Hall, Michael B. Journal of Organic Chemistry, 2000 , vol. 65, # 20 p. 6601 - 6612

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Citation Number: 23

Abstract

α, β-Unsaturated thioaldehydes and thioketones, R1CH CH-C (S) R2, are prepared in situ by the reaction between the corresponding carbonyl compounds and bis (dimethylaluminum) sulfide. These compounds undergo [4+ 2] self-dimerization reactions in which one molecule serves as the heterodiene component and the other as the dienophile to afford different types of dimeric products depending on the R1 and R2: 1, 2-dithiin and 1 ...