Reactions of Organic Anions, 177. Vicarious Nucleophilic Substitution of Hydrogen, Bisannulation and Competitive Reactions of α‐Haloalkyl Carbanions with Bicyclic Azaaromatic Compounds

Abstract

Abstract Carbanions of α‐haloalkyl aryl sulfones, sulfonates, and sulfonamides react with bicyclic heteroaromatic compounds (quinoxalines, naphthyridines, and 5‐azaquinoxalines) according to two general pathways: vicarious nucleophilic substitution of hydrogen and/or bisannulation. In some cases other competitive reactions such as S N Ar are observed. Factors governing the direction of these reactions are discussed in terms of the charge distribution in the anionic σ adducts and the reaction conditions.