Reaction of Difluoromethyl Phenyl Selenoxide with Acetic Anhydride. A Route to Difluoro(phenylseleno)methylation of Ethers
作者:Kenji Uneyama、Kazuhiro Maeda、Yukio Tokunaga、Nobuaki Itano
DOI:10.1021/jo00107a016
日期:1995.1
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 omega-[difluoro(phenylseleno)methoxy]alkyl acetates 4 in 34-87% 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 phenylselenenyl acetate is proposed.