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Trapping of Payne rearrangement intermediates with arylselenide anions

Published Web Location

https://doi.org/10.1016/j.tetlet.2014.11.103
Abstract

© 2014 Elsevier Ltd. The intermediate epoxy alcohols prepared via a Payne rearrangement can be trapped with arylselenide anions, giving mixtures of ring-opened products. The 1-arylseleno-2,3-diols are generally favored over the 3-arylseleno-1,2-diols in this process although the reaction of trisubstituted epoxyalcohols, for example, 17, differs from those of disubstituted epoxyalcohols, for example, 21.

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