Tetrahedron

Reactions of ortho oxy-substituted benzyl and phenacyl bromides in dimethyl sulphoxide

JA Donnelly, PA Kerr, P O'Boyle

文献索引：Donnelly,J.A. et al. Tetrahedron, 1973 , vol. 29, p. 3979 - 3983

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被引用次数: 8

摘要

o-Acetoxy-and o-benzoyloxy-benzyl bromides and tosylates oxidatively rearrange in moist dimethyl sulphoxide to o-hydroxybenzyl esters; o-acetoxy-and o-benzoyloxy-phenacyl bromides rearrange to mixtures of 2-hydroxycoumaran-3-ones and o-hydroxyphenacyl esters; o-hydroxyphenacyl bromides also yield 2-hydroxycoumaran-3-ones, together with o- hydroxyphenacyl alcohols. 2-Acetoxybenzaldehyde is reductively rearranged by sodium ...