Studies on Organic Fluorine Compounds. 38. Ring-Opening Reactions of gem-Difluorocyclopropyl Ketones with Nucleophiles

Article abstract of DOI:10.1021/jo00138a006

Syntheses of gem-difluorocyclopropyl ketones (3a-d) and their reactions with nucleophiles are described.Ring-opening reaction of 3a,c,d having a hydrogen substituent at C₁ adjacent to the carbonyl group with a methanolate anion gave carboxylic acid derivatives derived from C₁-C₂ bond scission (between the carbon atom with an acyl group and the carbon atom with fluorine substituents).On the other hand, reaction of 3a-c with a thiolate anion resulted in the C₁-C₃ bond cleavage (carbon-carbon bond opposite to the difluoromethylene group).