Tetrahedron

A facile synthesis of naturally occurring binaphthoquinones: efficient oxidative dimerization of 4-alkoxy-1-naphthols using silver (II) oxide–40% nitric acid

…, M Hashimoto, S Morishita, M Hamada, N Kai, T Nagai

Index: Tanoue, Yasuhiro; Sakata, Kazunori; Hashimoto, Mamoru; Morishita, Shin-Ich; Hamada, Moritsugu; Kai, Norihisa; Nagai, Takeshi Tetrahedron, 2002 , vol. 58, # 1 p. 99 - 104

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Citation Number: 15

Abstract

Oxidation of 4-alkoxy-1-naphthols with AgO–40% HNO3 occurred along with a dimerization to give the corresponding bi-1, 4-naphthoquinones. The oxidative dimerization required one hydroxyl group and took place at its ortho position. This reaction was applicable to syntheses of naturally occurring binaphthoquinones, bivitamin K3 and 3, 3′-bijuglone.