A new method for the halogenation of olefinic bonds without the utilization of molecular halogens is described. This synthetic technique is based on the reaction of olefins with copper(II) halides in the presence of strong coordinating agents. Simple olefins are converted to vicinal dihaloalkanes in good to excellent yields. Conjugated diolefins experienced predominately 1,4 addition. Complexed copper(II) halides in combination with different halide donors afforded an in situ synthesis of pseudohalogen compounds, which yielded ultimately chloroiodoand chlorobromoalkanes. The general scope of these reactions has been demonstrated for a variety

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For cases such as 9a, synthesis is best accomplished by condensation with urethane followed by selective decarboxylation with methoxide; cf. T.

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