The Journal of Organic Chemistry

Metallo aldimines. 3. Coupling of lithium aldimines with aryl, vinyl, and acetylenic halides

MJ Marks, HM Walborsky

Index: Marks, Maurice J.; Walborsky, Harry M. Journal of Organic Chemistry, 1982 , vol. 47, # 1 p. 52 - 56

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Citation Number: 16

Abstract

tert-Butyllithium aldimine, an acyl anion equivalent derived from 1, 1, 3, 3-tetramethylbutyl isocyanide (TMBI) and tert-butyllithium, couples with aryl, vinyl, and acetylenic halides to give the corresponding ketimine which upon hydrolysis affords the corresponding ketones. These coupling reactions appear to result from halogen-metal exchange followed by addition-elimination to give the observed products.

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