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

K Uneyama, K Maeda, Y Tokunaga…

Index: Uneyama, Kenji; Maeda, Kazuhiro; Tokunaga, Yukio; Itano, Nobuaki Journal of Organic Chemistry, 1995 , vol. 60, # 2 p. 370 - 375

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Citation Number: 13

Abstract

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 Ac20 in refluxing dichloromethane to give w-[difluoro (phenylseleno) methoxyl-alkyl acetates 4 in 3447% yields. A sequential reaction of Pummerer type rearrangement, difluorocarbene formation, electrophilic addition of the ...