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The photolysis of anydro‐4‐hydroxy‐2,3,5‐triarylthiazolium hydroxides
Author(s) -
Sheradsky Tuvia,
Zbaida David
Publication year - 1983
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.5570200153
Subject(s) - chemistry , photodissociation , bicyclic molecule , methanol , lactam , hydroxide , medicinal chemistry , ring (chemistry) , alcohol , potassium hydroxide , aryl , stereochemistry , organic chemistry , alkyl
The photolysis of anhydro‐4‐hydroxy‐2,3,5‐triphenylthiazolium hydroxide and of two substituted derivatives in methanol or t ‐butyl alcohol in the presence of trimethylphosphite, leads exclusively and stereospecifically to α‐aryl‐β‐anilinocinnamate esters. A mechanism which involves ring contraction to a bicyclic β‐lactam is suggested.