Bromophilic substitution/carbophilic substitution cascade reactions of α, α-dibromo-2-methoxyacetophenone with C-, N-and O-nucleophiles

…, R Marković, M Stojanović, M Baranac-Stojanović

Index: Tatar, Jovana; Markovic, Rade; Stojanovic, Milovan; Baranac-Stojanovic, Marija Tetrahedron Letters, 2010 , vol. 51, # 37 p. 4851 - 4855

Full Text: HTML

Citation Number: 5

Abstract

α, α-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford α-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1, 1, 3, 3-tetracyanopropene is obtained.