A Facile Synthesis of gem-Difluorinated Heterocyclic Compounds Using Anodic­ Fluorination of 2-Cyano-1-methylpyrrole as a Key Step

Toshiki Tajima; Toshio Fuchigami

doi:10.1055/s-2002-35621

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Synthesis 2002(17): 2597-2600
DOI: 10.1055/s-2002-35621

SPECIALTOPIC

A Facile Synthesis of gem-Difluorinated Heterocyclic Compounds Using Anodic Fluorination of 2-Cyano-1-methylpyrrole as a Key Step

Toshiki Tajima, Toshio Fuchigami*
Department of Electronic Chemistry, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 226-8502, Japan
Fax: +81(45)9245406; e-Mail: fuchi@echem.titech.ac.jp;

Further Information

Publication History

Received 23 September 2002
Publication Date:
20 November 2002 (online)

Abstract
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Abstract

Anodic fluorination of 2-cyano-1-methylpyrrole 1 using Et₃N·5HF in an undivided cell provided 5,5-difluoro-1-methyl-3-pyrrolin-2-one (5a). The Diels-Alder reaction of 5a with various dienes was successfully carried out to provide gem-difluorinated heterocyclic compounds in excellent yields.

Key words

anodic fluorination - 5,5-difluoro-1-methyl-3-pyrroline-2-one - gem-difluoromethylenes - Diels-Alder reaction - dienes

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