Oxyanionic substituent effect on the carbon-hydrogen insertion of carbenes. Reaction of alkoxides with dichlorocarbene and chlorophenylcarbene

T Harada, E Akiba, A Oku

Index: Harada, Toshiro; Akiba, Eiji; Oku, Akira Journal of the American Chemical Society, 1983 , vol. 105, # 9 p. 2771 - 2776

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Citation Number: 2

Abstract

Abstract: The lithium alkoxides of benzylic, allylic, and simple alkyl alcohols were allowed to react with chloroform in the presence of t-BuOLi in THF-hexane to give, in 32-91% yields, dichloromethylcarbinols, which were produced by the insertion of dichlorocarbene into the a CH bond of alkoxides but not by the Wittig rearrangement of carbanions of alkyl dichloromethyl ethers. The enhanced reactivity toward dichlorocarbene of the a CH bond ...