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1,3‐Dithioles and 1,3‐dithiole‐s‐oxides
Author(s) -
Campaigne E.,
Haaf F.
Publication year - 1964
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.5570010401
Subject(s) - chemistry , dithiol , oxalyl chloride , hydrogen chloride , hydrogen peroxide , condensation , medicinal chemistry , chloride , organic chemistry , physics , thermodynamics
1,3‐Dithioles have been prepared by a new route from α‐haloketones and a gem ‐dithiol. The reaction was carried out with aliphatic and aromatic α‐haloketones, which were condensed with 1,3‐diphenylpropane‐2,2‐dithiol to give 2,2‐dibenzyl‐4‐hydroxy‐1,3‐dithiolanes. These intermediates were dehydrated in the presence of acids to 2,2‐dibenzyl‐1, 3‐dithioles. Two of the 2,2‐dibenzyl‐1,3‐dithioles were oxidized with hydrogen peroxide to the corresponding S‐dioxides, S‐trioxides, and S‐tetroxides, which were separated by preparative thin layer chromatography. The condensation of 1,3‐diphenylpropane‐2, 2 ‐ dithiol with oxalyl chloride gave 2, 2‐dibenzyl‐1, 3‐dithiolane‐4, 5‐dione. Infrared and n.m.r. data of these compounds confirm the structural assignments.