Tetrahedron

Quinones and quinone methides—V: Further rearrangements of the dimer from 5-methoxy-2-(4-methoxyphenylmethyl)-1, 4-benzoquinone

L Jurd, JN Roitman

Index: Jurd,L.; Roitman,J.N. Tetrahedron, 1979 , vol. 35, p. 1567 - 1574

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Citation Number: 8

Abstract

In strongly acid solutions the dimer 3 dissociates to the quinone 1 and quinone methide 2 which recombine with elimination of p-methoxybenzyl alcohol to form the xanthylium salt 9a. With zinc and acetic acid 3 yields isormeric meso-and dl-ethylenediquinol derivatives 14a. Sodium borohydride reduction of 3 yields an alcoholic quinol 5a which rapidly reoxidizes to the spiro-tetrahydrofuran derivative 24a. Possible mechanisms which may be involved in ...