Reactions of ortho oxy-substituted benzyl and phenacyl bromides in dimethyl sulphoxide |
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| Authors: | JA Donnelly PA Kerr P O&#x;Boyle |
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| Institution: | Chemistry Department, University College, Dublin 4, Ireland |
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| Abstract: | 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 borohydride to o-hydroxybenzyl acetate. |
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