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Synlett 1991; 1991(12): 909-910
DOI: 10.1055/s-1991-20920
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A Facile Synthesis of Difluoromethylene Compounds by Oxidative Fluorodesulfurization of Dithioacetals Using Tetrabutylammonium Dihydrogentrifluoride and N-Halo Compounds

Manabu Kuroboshi* , Tamejiro Hiyama
  • *Sagami Chemical Research Center, Nishiohnuma 4-4-1, Sagamihara, Kanagawa 229, Japan
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Publication Date:
07 March 2002 (online)

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Cyclic dithioacetals of aldehydes and ketones are converted into the corresponding difluoromethylene compounds with characteristic chemoselectivity by means of tetrabutylammonium dihydrogen trifluoride and N-halo amides or imides (N-bromosuccinimide, N-iodosuccinimide and 1,3-dibromo-5,5-dimethylhydantoin) in good to excellent yield. The substrates which have an acid-sensitive functionality or other easily fluorinated functionalities give the desired products without any damage to that functionality.

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