Synthesis of 5, 7-dihydroxynaphthoquinone derivatives and their reactions with nucleophiles: Nitration of 2, 3-dimethylnaphthalene and subsequent transformations

HJ Banks, DW Cameron, MJ Crossley…

Index: Banks,H.J. et al. Australian Journal of Chemistry, 1976 , vol. 29, p. 2247 - 2256

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Abstract

Abstract 5, 7-Dihydroxy-2, 3-dimethyl-l, 4-naphthoquinone (5) and related compounds have been synthesized. The quinone affords an accessible substrate for studying an unusual reaction with nucleophiles, which involves attack at the 8-position, ie at the benzenoid ring. An unsuccessful approach to (5) has led to tri-and tetra-nitro derivatives of 2, 3- dimethylnaphthalene. Reduction of the former and subsequent conversions have given ...