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Heterocyclic tautomerisms. II. An investigation of the 2‐arylbenzothiazoline 2‐(benzylideneamino)thiophenol tautomerism. Part 2
Author(s) -
Goetz Frederick J.
Publication year - 1968
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.5570050410
Subject(s) - thiophenol , chemistry , tautomer , monomer , aldimine , medicinal chemistry , aryl , catalysis , polymer chemistry , organic chemistry , polymer , alkyl
The reaction between 4‐mercaptoaniline and various aromatic aldehydes was studied as a model system in order to determine which type of substitution on the aryl group in 2‐arylbenzothiazolines (1) might give rise to the greatest possible stabilization of the hypothetical 2‐(benzylideneamino)thiophenol tautomer (II). Regardless of electronic effect of substituents, most aldehydes reacted with 4‐mercaptoaniline to form poly[4‐(benzylideneamino)thiophenols] (III). Aromatic aldehydes substituted in the 2 position with the hydroxyl function reacted to form the stable, monomeric 4‐(benzylideneamino)thiophenols (IV). This stabilization in the monomeric state is presumed to be due to the hydrogen‐bonded nature of these compounds (V). Both monomeric and polymeric compounds reacted with benzalacetophenone in the presence of a basic catalyst in the manner to be expected of the 4‐(benzylideneamino)thiophenol structure (IV) yielding correspondingly substituted 1,3‐diphenyl‐1‐[4‐(benzylideneamino)phenylthio]‐3‐propanones (VI).