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The chemistry of a ketene‐sulfur dioxide adduct
Author(s) -
Gomes Ailton De Souza,
Joulliéa Madeleine M.
Publication year - 1969
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.5570060521
Subject(s) - chemistry , ketene , adduct , cycloaddition , sulfur dioxide , thiazolidine , aniline , medicinal chemistry , oxide , derivative (finance) , sulfur , organic chemistry , catalysis , financial economics , economics
We have demonstrated the formation of a reactive species from ketene and sulfur dioxide and have investigated some of its reactions. The 3 + 2 ← 5 cycloaddition reactions of this intermediate with benzylideneaniline and its derivatives gave the corresponding 2,3‐diphenylthiazolidin‐4‐one 1,1‐dioxides. The reduction of 2,3‐diphenylthiazolidin‐4‐one 1,1‐dioxide with lithium aluminum hydride yielded the corresponding thiazolidine. Aniline and its derivatives reacted with the ketene‐sulfur dioxide adduct to give thioaceto‐1,3‐dianilide 3‐oxide. o ‐Phenylenediamine gave [2,1,5]benzothiadiazepin‐4‐one 2‐oxide, a derivative of a new ring system, [2,1,5]benzothiadiazepine. o ‐Aminophenol yielded [1,2,5]benzothiazepin‐4‐one 2‐oxide.