Synthesis of (p-Nitroaryl)diarylmethanes via Vicarious Nucleophilic Substitution of Hydrogen

M. Makosza; M. Surowiec; S. Voskresensky

doi:10.1055/s-2000-6411

Synthesis 2000; 2000(9): 1237-1240
DOI: 10.1055/s-2000-6411

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Synthesis of (p-Nitroaryl)diarylmethanes via Vicarious Nucleophilic Substitution of Hydrogen

M. Ma˛kosza^* , M. Surowiec, S. Voskresensky

^*Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL-01-224 Warsaw, Poland; Fax + 48(22)6 32 66 81; E-mail: icho-s@icho.edu.pl

Abstract

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(p-Nitroaryl)diarylmethanes are readily prepared via vicarious nucleophilic substitution of hydrogen in nitroarenes with carbanions of diarylmethyl p-chlorophenyl sulfide. These carbanions are efficient for introduction of diarylmethyl substituents in the para position of nitroarenes via the VNS reaction. The reaction does not proceed ortho to the nitro group due to steric hindrances on the addition step.

carbanions - vicarious nucleophilic substitution of hydrogen - sulfides - nitroarenes - arylations

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