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Successive Cycloadditions between 4‐Fluoro‐5‐trifluoromethyl‐1,2‐dithiole‐3‐thione and Dimethyl Acetylenedicarboxylate: New Fluorinated Thiaheterocycles through New Reaction Mechanisms
Author(s) -
Timoshenko Vadim M.,
Bouillon JeanPhilippe,
Chernega Alexander N.,
Shermolovich Yuriy G.,
Portella Charles
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300036
Subject(s) - dimethyl acetylenedicarboxylate , chemistry , cycloaddition , trifluoromethyl , medicinal chemistry , reaction mechanism , photochemistry , organic chemistry , catalysis , alkyl
The cycloaddition reaction between dimethyl 2‐(1‐fluoro‐2‐trifluoromethyl‐2‐thioxoethylidene)‐1,3‐dithiole‐4,5‐dicarboxylate and dimethyl acetylenedicarboxylate proceeds efficiently under irradiation conditions in air. A study of the reaction conditions resulted in the proposal of a chain mechanism initiated by a photochemically induced single‐electron transfer to oxygen. On the other hand, the cycloadduct can be transformed into a rearranged hydroxylated product by filtration through silica gel. Either the cycloadduct or its rearranged product can be obtained selectively in a one‐pot process from the parent 1,2‐dithiole‐3‐thione. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)