1986Angewandte Chemie International Edition in EnglishRequires access

Reactivity of Anionic Pentacoordinated Silicon Complexes towards Nucleophiles

Alain Boudin, Geneviève Cerveau, Claude Chuit, Robert J. P. Corriu, Catherine Reyé

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Abstract

Steric hindrance seldom plays a role in nucleophilic substitutions at silicon, since the pentacoordinated Si anions of 1, R, R = Me, Ph, 1-naphthyl, react far more rapidly with nucleophiles, e.g. PhMgBr, than the neutral compound 2. “By-products” of the reactivity study are new synthetic methods for RSiH3, RR′2SiH, and RSiR′3 (R′ = alkyl, aryl).

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What this paper is about

Steric hindrance seldom plays a role in nucleophilic substitutions at silicon, since the pentacoordinated Si anions of 1, R, R = Me, Ph, 1-naphthyl, react far more rapidly with nucleophiles, e.g. PhMgBr, than the neutral compound 2. “By-products” of the reactivity study are new synthetic methods for RSiH3, RR′2SiH, and RSiR′3 (R′ = alkyl, aryl).

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Available abstract

Steric hindrance seldom plays a role in nucleophilic substitutions at silicon, since the pentacoordinated Si anions of 1, R, R = Me, Ph, 1-naphthyl, react far more rapidly with nucleophiles, e.g. PhMgBr, than the neutral compound 2. “By-products” of the reactivity study are new synthetic methods for RSiH3, RR′2SiH, and RSiR′3 (R′ = alkyl, aryl).

Key concepts: Nucleophile, Steric effects, Reactivity (psychology), Chemistry, Alkyl, Aryl, Silicon, Medicinal chemistry

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