Reaction of phenyl-substituted allyllithiums with tert-alkyl bromides. Remarkable difference in the alkylation regiochemistry between a polar process and the one …

J Tanaka, M Nojima, S Kusabayashi

Index: Tanaka, Jiro; Nojima, Masatomo; Kusabayashi, Shigekazu Journal of the American Chemical Society, 1987 , vol. 109, # 11 p. 3391 - 3397

Full Text: HTML

Citation Number: 17

Abstract

Abstract: The reaction of phenyl-substituted allyllithiums la-h with tert-alkyl bromides was investigated systematically. The alkylation regiochemistry was influenced in a complicated fashion by various factors including substituent effects, both steric and electronic, solvents, and the presence of strongly coordinating additives, tetramethylethylenediamine and hexamethylphosphoramide. On the basis of the cyclizable probe experiments, the ...