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Synthesis and Addition Reactions of 1,3-Thiazole-5(4H)-thione Oxides

✍ Scribed by Junxing Shi; Peter Tromm; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1994
Tongue
German
Weight
584 KB
Volume
77
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

1,3‐Thiazole‐5(4__H__)‐thione oxides 2 were prepared by oxidation of the corresponding 1,3‐thiazole‐5(4__H__)‐thiones 1 with m‐chloroperbenzoic acid (Table 1). Addition reactions of 2 with organolithium and Grignard reagents yielded 4,5‐dihydro‐4,4‐dimethyl‐1,3‐thiazol‐5‐yl methyl sulfoxides of type 4 via thiophilic attack (Table 2). Whereas the reaction with the organolithium compounds proceeded with fair‐to‐excellent yields, the Grignard reagents reacted only very sluggishly. The sulfoxides 4 could also be prepared via oxidation of 4,5‐dihydro‐4,4‐dimethyl‐5‐(methylthio)‐1,3‐thiazoles of type 3 with m‐chloroperbenzoic acid, together with the corresponding sulfones 5 (Scheme 1).

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