New methodology for the deoxygenative difluoromethylenation of aldehydes and ketones; unexpected formation of tetrafluorocyclopropanes.
Generation of difluoromethylene phosphorus ylides in the presence of aldehydes and ketones results in Wittig-type reactions to give gem-difluoroalkenes. Subsequent in situ addition of difluorocarbene (carbenoid) can occur (increased with triphenylphosphine and decreased with tributylphosphine) to give tetrafluorocyclopropanes. [Reaction: see text]
Nowak
Ireneusz
I
Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602-5700, USA.
Robins
Morris J
MJ
D000447:Aldehydes / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis*; D005459:Fluorides; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure
D000447:Aldehydes; D003521:Cyclopropanes; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D005459:Fluorides