Tetrahedron

Vicarious nucleophilic substitution of hydrogen (VNS) in 1, 4-naphthoquinone derivatives—competition between VNS and vinylic nucleophilic substitution (SNV)

M Mąkosza, S Nizamov

Index: Makosza, Mieczyslaw; Nizamov, Shamil Tetrahedron, 2001 , vol. 57, # 47 p. 9615 - 9621

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Citation Number: 16

Abstract

Carbanions of dimethyl chloromalonate, ethyl 2-chloroacetoacetate and dimethyl malonate react with naphthoquinone derivatives mainly via vicarious nucleophilic substitution or oxidative nucleophilic substitution of hydrogen processes. These reactions in 2-halo substituted naphthoquinones are generally faster processes than vinylic nucleophilic substitution of halogen (SNV). Introduction of one Cl substituent into position 2-of 1, 4- ...