Tetrahedron

One-pot dialkylation of allylphenylsulfide induced by aminoalkoxides-activated NaNH 2. Application to the synthesis of unsymmetrical ketones

S Choppin, P Gros, Y Fort

Index: Choppin, Sabine; Gros, Philippe; Fort, Yves Tetrahedron, 1999 , vol. 55, # 30 p. 9261 - 9268

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Citation Number: 3

Abstract

It is shown that the activation of NaNH2 by sodium aminoalkoxides, leading to new superbases, induced an efficient one-pot dialkylation of allylphenylsulfide. The regioselectivity of the reaction (α, α′ vs α, γ) was found as strongly dependent on the nature of the alkyl halide. As an application, α, γ dialkylated products were efficiently converted into the corresponding unsymmetrical ketones.

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