Journal of the American Chemical Society

3, 3-Dimethylallenyllithium. Reaction with electrophiles leading to carbenoid, electron transfer, and nucleophilic processes

X Creary

Index: Creary,X. Journal of the American Chemical Society, 1977 , vol. 99, # 23 p. 7632 - 7639

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Citation Number: 61

Abstract

Abstract: Reaction of lithium dialkylamide bases with a benzyl halide-3, 3-dimethylallene (1) mixture gave aryl carbenoid addition products via deprotonation of the benzyl halide. Competing deprotonation of 1 also occurs giving 3, 3-dimethylallenyllithium (8). Products of reaction of 8 with benzyl halides were acetylenes (major) and allenes (minor) and were rationalized in terms of an electron transfer mechanism leading to the 3, 3-dimethylallenyl ...