Reactions of Trimethylstannyl Ions with Mono-, Di- and Trichloro-Substituted Aromatic Substrates by the SRN1 Mechanism

Eduardo F. Córsico; Roberto A. Rossi

doi:10.1055/s-2000-6502

Synlett 2000; 2000(2): 227-229
DOI: 10.1055/s-2000-6502

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Reactions of Trimethylstannyl Ions with Mono-, Di- and Trichloro-Substituted Aromatic Substrates by the S_RN1 Mechanism

Eduardo F. Córsico^* , Roberto A. Rossi

^*INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina; Fax +54-3 51-4 33 30 30; E-mail: rossi@dqo.fcq.unc.edu.ar

Abstract

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The reactions of Me₃Sn^- ion with 2-chloropyridine, p-chlorobenzonitrile, o-, m-dichlorobenzenes, 1,3,5-trichlorobenzene, 2,5-, 2,6-, and 3,5-dichloropyridines give good yields of substitution products. When p-bis-(trimethylstannyl)benzene is treated with Na metal in liquid ammonia, a dianion is formed, which upon photostimulated reaction with PhCl, affords the disubstitution product in 70% yield. We suggest that all these reactions occur by the S_RN1 mechanism of nucleophilic substitution.

Bis(trimethylstannyl)benzenes - bis(trimethylstannyl)pyridines - photostimulation - tin nucleophiles - S_RN1 reactions

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