Formation of reactive o-quinone methides from the reaction of trimethylsilyl(methyl)-substituted 1,4-benzoquinones with nucleophiles |
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Authors: | John E. Ezcurra Kostas Karabelas Harold W. Moore |
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Affiliation: | Department of Chemistry, 516 Rowland Hall, The University of California, Irvine, CA 92697, USA |
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Abstract: | o-Quinone methides are formed from the reaction of nucleophiles with trimethylsilyl(methyl)-1,4-benzoquinones. These reactive intermediates are trapped by excess nucleophile to form substituted quinones following oxidation. In addition, varying amounts of a symmetrical dimer and a xanthen derivative were observed. The influence of different nucleophiles and ring substituents on the rate of reaction have been studied, and are consistent with rate-limiting formation of a vinylogous enolate initiated by attack of the nucleophile on the silyl group. |
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Keywords: | o-Quinone methide 1,4-benzoquinones Trimethylsilyl Michael addition Diels-Alder Dimerization |
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