The reaction of excess phenylselenenyl halides with trisubstituted cyclic olefins in aqueous acetonitrile is regio- and stereospecific and affords trans halohydrins in excellent yields. The reaction proceeds through the formation of a β-hydroxyalkyl phenyl selenide which evolves to halohydrin presumably via an epoxy-intermediate.
Trans 1,2-Functionalization of Cycloalkenes Using Selenium Intermediates
CECCHERELLI, Paolo;CURINI, Massimo;MARCOTULLIO, Maria Carla;ROSATI, Ornelio
1989
Abstract
The reaction of excess phenylselenenyl halides with trisubstituted cyclic olefins in aqueous acetonitrile is regio- and stereospecific and affords trans halohydrins in excellent yields. The reaction proceeds through the formation of a β-hydroxyalkyl phenyl selenide which evolves to halohydrin presumably via an epoxy-intermediate.File in questo prodotto:
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