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The thermal rearrangement of thiabenzenes to their isomeric thiopyrans
Author(s) -
Pirelahi Hooshang,
Haghgooii Housane
Publication year - 1979
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.5570160517
Subject(s) - chemistry , thiopyran , intramolecular force , aryl , medicinal chemistry , rearrangement reaction , tris , stereochemistry , organic chemistry , catalysis , alkyl , biochemistry
The rates of rearrangement in 1‐phenyl‐2,4,6‐tris( p ‐methoxyphenyl)thiabenzene (4) and 1‐( p ‐tri‐fluoromethylphenyl)‐2,4,6‐triphenylthiabenzene (5) were determined and a crossover experiment was carried out with a mixture of these thiabenzenes. The possibility of 2,4‐migrations in the thiopyran system under the reaction conditions was also studied by examining two samples of thiopyrans. The results indicate an intramolecular rearrangement which involves a 1,2‐ and 1,4‐migration of 5‐aryl groups in thiabenzenes.