1987•Liebigs Annalen der ChemieRequires access

Reactions of Organic Anions, 142. Reactions of α‐Chloroalkyl Sulfones with Nitronaphthalene Derivatives

Mieczysław Mąkosza, Witold Danikiewicz, Krzysztof Wojciechowski

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Abstract

Abstract 1‐and 2‐nitronaphthalene derivatives react with the carbanions derived from chloromethyl p‐tolyl sulfone and tert‐butyl chloromethyl sulfone to give products of the vicarious nucleophilic substitution of hydrogen predominantly or exclusively in position 2 and 1, respectively. A different orientation pattern and sometimes other reaction pathways are observed in the reactions involving tertiary carbanions derived from α‐chloropropyl p‐tolyl sulfone.

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Abstract 1‐and 2‐nitronaphthalene derivatives react with the carbanions derived from chloromethyl p‐tolyl sulfone and tert‐butyl chloromethyl sulfone to give products of the vicarious nucleophilic substitution of hydrogen predominantly or exclusively in position 2 and 1, respectively. A different orientation pattern and sometimes other reaction pathways are observed in the reactions involving tertiary carbanions derived from α‐chloropropyl p‐tolyl sulfone.

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Available abstract

Abstract 1‐and 2‐nitronaphthalene derivatives react with the carbanions derived from chloromethyl p‐tolyl sulfone and tert‐butyl chloromethyl sulfone to give products of the vicarious nucleophilic substitution of hydrogen predominantly or exclusively in position 2 and 1, respectively. A different orientation pattern and sometimes other reaction pathways are observed in the reactions involving tertiary carbanions derived from α‐chloropropyl p‐tolyl sulfone.

Key concepts: Carbanion, Sulfone, Chemistry, Nucleophile, Substitution reaction, Medicinal chemistry, Organic chemistry, Catalysis

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