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

Makosza Mieczyslaw | Zendy; Golinski Jerzy | Zendy; Ostrowski Stanislaw | Zendy; Sahasrabudhe Arvind B. | Zendy; Rykowski Andrzej | Zendy

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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.

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