Rearrangement of 1??aryl??2, 2??Dichloro??1??Alkanones and 1??Aryl??2, 2??Dichloro??1??Alkanols with Methylmagnesium Iodide

N de Kimpe, R Verhé, L de Buyck…

Index: de Kimpe,N. et al. Bulletin des Societes Chimiques Belges, 1979 , vol. 88, p. 719 - 735

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Abstract

Abstract 1-Aryl-2, 2-dichloro-1-alkanones were shown to rearrange with methyl magnesium iodide in ether under reflux into highly sterically hindered alkohols. The mechanism proceeds by a pseudo pinacol type rearrangement of the initially formed carbonyl adduct. The mechanism of the rearrangement was proven by the synthesis of authentic reaction intermediates. The rearrangement was also extended to 1-aryl-2, 2-dichloro-1-alkanols ...

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