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 SNAr 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.
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