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Photocycloaddition of Benzothiazole-2-thiones to Alkenes

✍ Scribed by Takehiko Nishio; Yo-Ichi Mori; Ikuo Iida; Akira Hosomi

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

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✦ Synopsis

Abstract

The photocycloaddition of benzothiazole‐2‐thiones to electron‐rich and aryl‐substituted alkenes are described. Irradiation of N‐unsubstituted benzothiazole‐2‐thione (1) in the presence of alkenes 3 gave 2‐(2′‐mercaptoalkyl)benzothiazoles 4, and 2‐substituted benzothiazoles 5 and 6 (in the case of 3a and 3h, resp.) through the ring cleavage of an intermediate 2‐aminothietane (Schemes 1 and 3). The latter was formed by [2+2] cycloaddition of the CS bond of 1 and the CC bond of 3. Irradiation of N‐methylbenzothiazole‐2‐thione (2) and 2‐methylpropene (3a) gave the spiro‐1,3‐dithiane 8, 1,2,6‐benzodithiazocin‐5‐one 9, and disulfide 10. The structure of 9 was established by X‐ray crystal‐structure analysis.

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