Nucleophilic Desulfinylation of [alpha]-Fluoro-[beta]-(alkoxy and silyloxy) Sulfoxides.Effects of the [beta]-Oxy Substituents on Protonation, 1,2-Hydrogen Migration, and Nucleophile Addition to the Fluorocarbenoid Centers

• Published in: Bulletin of the Chemical Society of Japan Vol. 65; no. 1; p. 218
• Main Authors: Uno, Hidemitsu, Sakamoto, Katsuji, Suzuki, Hitomi
• Format: Journal Article
• Language: English
• Published: Tokyo Chemical Society of Japan 01.01.1992

Treatment of 2-(4-biphenylyl)-2-t-butyldimethylsilyloxy-1-chloro-1-fluoroethyl phenyl sulfoxide with PhMgBr resulted in the formation of a fluorostilbene derivative, a fluoro enol silyl ether and small amounts of 4-(fluoroacetyl)biphenyl, while a similar reaction of 2-methoxymethoxy analog mainly le...