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Reactions of Organic Anions, 177. Vicarious Nucleophilic Substitution of Hydrogen, Bisannulation and Competitive Reactions of α‐Haloalkyl Carbanions with Bicyclic Azaaromatic Compounds
Author(s) -
Makosza Mieczyslaw,
Golinski Jerzy,
Ostrowski Stanislaw,
Sahasrabudhe Arvind B.,
Rykowski Andrzej
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240325
Subject(s) - carbanion , chemistry , bicyclic molecule , adduct , nucleophile , nucleophilic substitution , medicinal chemistry , aryl , organic chemistry , catalysis , alkyl
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.