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2005
Halogen compounds
Q 0090
New Methodology for the Deoxygenative Difluoromethylenation of Aldehydes and
Unexpected Formation of Tetrafluorocyclopropanes. — The conversion
27- 074 Ketones;
of carbonyl compounds into alkenes (and dienes) with a difluoromethylene terminus is
accompanied by formation of tetrafluorocyclopropane adducts. The reaction proceeds
in the presence of Hg(CF3)2 and tributyl- or triphenylphosphine. Difluoromethylene
phosphorus ylides are generated in situ, followed by Wittig-type reactions which afford
the gem-difluoroalkenes. Further addition of difluorocarbene causes formation of the
cyclopropanes. — (NOWAK, I.; ROBINS*, M. J.; Org. Lett. 7 (2005) 4, 721-724;
Dep. Chem. Biochem., Brigham Young Univ., Provo, UT 84602, USA; Eng.) —
Steudel
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