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Synlett 1996; 1996(3): 243-245
DOI: 10.1055/s-1996-5393
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The Reaction of 2,2-Difluorovinyl Ketones with Amines: A Facile Method for Preparation of α-Oxoketenimines and Acetoacetylation of Amines

Junji Ichikawa1 , Naoyuki Yokota, Masakuni Kobayashi, Kazuhiro Amano, Toru Minami2
  • 1Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan, Fax 81 93 884 3314, Bitnet ichikawa@post.isct.kyutech.ac.jp
  • 2Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan, Fax 81 93 884 3314
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Publication History

Publication Date:
31 December 2000 (online)

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2,2-Difluorovinyl ketones readily react with primary amines to afford α-oxoketenimines in good to high yields via double dehydrofluorination. Combined with succeeding hydrolysis, the reaction provides a facile method for acetoacetylation of primary and secondary amines.

2,2-difluorovinyl ketone - addition-elimination - α-oxoketenimine - acetoacetylation - β-oxoamide