Rearrangement of 2-Bromo-1-(bromomethyl)ethyl Esters Under Basic Conditions: Scope and Mechanism

Abstract

A novel rearrangement of 2-bromo-1-(bromomethyl)ethyl esters into the corresponding 2-oxopropyl derivatives is reported. The mechanism of this transformation was studied by means of ¹⁸O- and ²H-labeling experiments. The reaction proceeds through a transient dioxolane intermediate that is hydrolyzed to form the corresponding 2-oxopropyl acetate.

Key words

esters - halogens - ketones - rearrangements

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