Quinones and quinone methides—V: Further rearrangements of the dimer from 5-methoxy-2-(4-methoxyphenylmethyl)-1,4-benzoquinone |
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Authors: | L Jurd JN Roitman |
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Institution: | Western Regional Research Laboratory, Science and Education Administration, U.S. Department of Agriculture, Berkeley, CA 94710, U.S.A. |
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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 the formation of these rearranged products are discussed. |
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