Successive Cycloadditions between 4‐Fluoro‐5‐trifluoromethyl‐1,2‐dithiole‐3‐thione and Dimethyl Acetylenedicarboxylate: New Fluorinated Thiaheterocycles through New Reaction Mechanisms | Zendy

Timoshenko Vadim M. | Zendy; Bouillon JeanPhilippe | Zendy; Chernega Alexander N. | Zendy; Shermolovich Yuriy G. | Zendy; Portella Charles | Zendy

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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)

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