Trapping of Payne rearrangement intermediates with arylselenide anions
Published Web Locationhttps://doi.org/10.1016/j.tetlet.2014.11.103
© 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.