Selectivities in reactions of organolithium reagents with aryl bromides which bear proton-donating groups

P Beak, TJ Musick, C Liu, T Cooper…

Index: Beak, Peter; Musick, Timothy J.; Liu, Chao; Cooper, Thomas; Gallagher, Donald J. Journal of Organic Chemistry, 1993 , vol. <26> 58, p. 7330 - 7335

Full Text: HTML

Citation Number: 24

Abstract

Studies of substrates which offer an acidic hydrogen and an aryl bromide for reaction with an organolithium reagent have been carried out with a series of benzene bromo amides and bromo anilide8 as well as selected benzene bromo carboxylic acids, bromoanilines, and bromobenzylamines. A representative example is the reaction of N-ethyl-N-deutero-o- bromobenzamide (6-d) with 1-lithio-3-phenylpropane to giveN-ethyl-o-deuterobenzamide ...