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 18 O- and 2 H-labeling experiments. The reaction proceeds through a transient dioxolane intermediate that is hydrolyzed to form the corresponding 2-oxopropyl acetate.

This novel rearrangement of 2-bromo-1-(bromomethyl)ethyl esters into 2-oxopropyl derivatives occurs under basic conditions, with a transient dioxolane intermediate and hydrolysis to form 2-oxopropyl acetate.

Paper

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

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