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Base-catalyzed rearrangement of alpha-benzotriazolyl alkoxide anions: Synthesis of one-carbon homologated alpha-substituted alkyl ketones
Journal article   Peer reviewed

Base-catalyzed rearrangement of alpha-benzotriazolyl alkoxide anions: Synthesis of one-carbon homologated alpha-substituted alkyl ketones

A R Katritzky, Z X Zhang, H Y Lang and L H Xie
Heterocycles, Vol.47(1), pp.187-194
01/01/1998

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
Deprotonated benzotriazole derivatives (la-c) reacted with aldehydes to give the alpha-oxyanion substituted intermediates (2), which upon further treatment with butyllithium, without separation, resulted in the formation of one-carbon homologated a-substituted alkyl ketones (6a-f). Similar treatment of benzotriazole derivatives (1d-f) generated the benzotriazole ring-opening and rearranged products (7a-f). Plausible mechanisms for these reactions have been proposed.

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