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Synlett 1997; 1997(10): 1159-1160
DOI: 10.1055/s-1997-981
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Synthesis of Mono-Fluorinated Quinones by an Unusual SRN1 Reaction: Difluoromethyl Quinones as Substrates

Anne Giraud1 , Luc Giraud2 , Michel P. Crozet3 , Patrice Vanelle4
  • 1Institut de Chimie Organique, Université de Fribourg, Pérolles, CH-1700 Fribourg, Switzerland
  • 2Institut de Chimie Organique, Université de Fribourg, Pérolles, CH-1700 Fribourg, Switzerland, Fax (41) 26 300 97 39; E-mail: luc.giraud@unifr.ch
  • 3LCMO, UMR 6517, CNRS-Universités d’Aix-Marseille I et III, B.P. 562, 13397 Marseille Cedex 20, France
  • 4Laboratoire de Chimie Organique, Faculté de Pharmacie, 27 Bd J. Moulin, 13385 Marseille Cedex 05, France
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Publication History

Publication Date:
31 December 2000 (online)

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Aldehydes are transformed into stable gem-difluoro compounds. Upon standard SRN1 reaction conditions, they generate anion radicals that undergo a very fast fluoride elimination to produce methylene quinones which are alkylated by a nucleophile. This process gives rise to facile access to new fluorinated species having any side chain. It is the first reported example of gem-difluoro compounds reacting by the SRN1 mechanism.

gem-difluoroquinones - ortho-methylenequinones - anion radicals - SRN1 reaction

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