Journal of the American Chemical Society

Halogen-Metal Interchange Reactions of 3, 3, 3-Trichloro-1, 2-epoxypropane and of Chloral with Organolithium Compounds and Grignard Reagents

W Reeve, LW Fine

Index: Reeve,W.; Fine,L.W. Journal of the American Chemical Society, 1964 , vol. 86, p. 880 - 882

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Citation Number: 15

Abstract

Phenyllithium was allowed to react with the epoxide I under the same experimental conditions. Again, 3, 3-dichloroallyl alcohol was obtained (81% yield). Chlorobenzene was isolated in 68y0 yield. In the above two cases, the halogen-metal interchange reaction must be much faster than the attack of a strongly nucleophilic ion on the epoxide ring, for in each case a halide ion was present from the preparation of the organolithium reagent-bromide ...