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On the syntheses and some reactions of bis‐ and tris(methylthio)thiophenes
Author(s) -
Gronowitz Salo,
Temciuc Marcel,
Hörnfeldt AnnaBritta
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300448
Subject(s) - chemistry , thiophene , tris , halogenation , medicinal chemistry , organic chemistry , ethyl chloroformate , biochemistry
Reaction between various thienyllithium derivatives and dimethyl disulfide has been used for the preparation of 2,5‐, 2,3‐, and 3,4‐bis(methylthio)thiophenes, as well as 2,3,4‐ and 2,3,5‐tris(methylthio)thiophenes. Bromination of (methylthio)thiophenes with N ‐bromosuccinimide was found to be most convenient for the preparation of brominated (methylthio)thiophenes such as 3‐bromo‐2,5‐bis(methylthio)‐ and 5‐bromo‐2,3‐bis(methylthio)thiophene, 3,4‐dibromo‐2,5‐bis(methylthio)‐, 2,5‐dibromo‐3,4‐bis(methylthio)‐ and 2,3‐dibromo‐4,5‐bis(methylthio)thiophene as well as 3‐bromo‐2,4,5‐tris(methylthio)thiophene. The reaction of methylthio substituted thienyllithium derivatives with methyl chloroformate was used for the syntheses of methyl methylthio substituted thiophenecarboxylates and using 1/3 of an equivalent for the direct preparation of methylthio substituted 3‐thienylcarbinols as tris[2,4,5‐tris(methylthio)‐3‐thienyl]carbinol.