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Mechanism of formation of benzothiazole‐2‐thiol
Author(s) -
Isaacs Neil S.,
Ismail Fyaz,
Hilton Mark J.,
Coulson Mark
Publication year - 1998
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199801)11:1<1::aid-poc964>3.0.co;2-#
Subject(s) - chemistry , benzothiazole , mechanism (biology) , thiol , combinatorial chemistry , computational chemistry , organic chemistry , epistemology , philosophy
The formation of benzothiazole‐2‐thiol from aniline, carbon disulphide and sulphur at 230°C was shown to occur by a sequence of three principal steps. Labelling experiments confirmed that both sulphur atoms originate from carbon disulphide. An initial polar reaction to form thiocarbanilide via phenylcarbamic acid and a tetrahedral intermediate is followed by radical cyclization of these to benzothiazole‐2‐thiol and 2‐phenylaminobenzothiazole; the latter is converted into the desired product by a polar displacement of aniline by H 2 S. Mechanisms for the formation of minor byproducts are also considered. © 1998 John Wiley & Sons, Ltd.