A novel method for the direct conversion of some substituted ethylenes to ketones is described. The ketone synthesis is shown to proceed with a concurrent rearrangement of the carbon skeleton. A mechanism, supported by isotopic labeling experiments, is postulated to account for the transformation.The addition of bromine to olefins is a well-known reaction frequently used as a qualitative test for unsaturation.The products of such additions are usually the corresponding dibromides. However, in at least two reported4•5 instances ketones have been isolated as by-products.
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