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Photocycloaddition of Benzothiazole‐2‐thiones to Alkenes
Author(s) -
Nishio Takehiko,
Mori YoIchi,
Iida Ikuo,
Hosomi Akira
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770410
Subject(s) - benzothiazole , chemistry , cycloaddition , ring (chemistry) , crystal structure , medicinal chemistry , disulfide bond , cleavage (geology) , stereochemistry , aryl , crystallography , organic chemistry , catalysis , alkyl , biochemistry , geotechnical engineering , fracture (geology) , engineering
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 CS bond of 1 and the CC 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.