4.4 Article

Photodegradation of 2-mercaptobenzothiazole disulfide and related benzothiazoles

Journal

JOURNAL OF HETEROCYCLIC CHEMISTRY
Volume 45, Issue 2, Pages 303-306

Publisher

HETERO CORPORATION
DOI: 10.1002/jhet.5570450201

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The photodegradation of 2-mercaptobenzothiazole disulfide, 2-mercaptobenzothiazole and benzothiazole was investigated. Benzothiazole was found to undergo photodimerization into 2,2'-bibenzothiazole, and in the presence of oxygen to give two additional photoproducts - 2-hydroxybenzothiazole and 2-methylbenzothiazole. The major degradation products of 2-mercaptobenzothiazole are benzothiazole and 2-benzothiazolesulfonic acid, with 2,2'-thiobisbenzothiazole and 2-mercaptobenzothiazole disulfide as the minor degradation products. Direct photolysis of 2-mercaptobenzothiazole disulfide gave 2-mercaptobenzothiazole and in acetonitrile 2-thiocyanatobenzothiazole was also detected. A mechanism is proposed to rationalize the formation of photodegradation products.

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