Reaction of Difluoromethyl Phenyl Selenoxide with Acetic Anhydride. A Route to Difluoro(phenylseleno)methylation of Ethers

Article abstract of DOI:10.1021/jo00107a016

Difluoromethyl phenyl selenoxide (2) has been prepared and allowed to react with acetic anhydride in the presence of cyclic ethers and sulfides.Difluorophenylselenomethylation occurred smoothly on reacting 2 with Ac2O in refluxing dichloromethane to give ω-alkyl acetates 4 in 34-87percent yields.A sequential reaction of Pummerer type rearrangement, difluorocarbene formation, electrophilic addition of the carbene to oxygen of ethers leading to oxonium ylide, and trapping with phenylselenyl acetate is proposed.