ORGANIC DEUTERIUM COMPOUNDS: XXIII. SYNTHESIS OF DEUTERATED OLEFINS

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Abstract
The synthesis of some deuterated ethylenes, propylenes, butenes, and pentenes is described. Homolytic addition of hydrogen bromide and deuterium bromide to allene and some deuteroallenes was investigated and found to give 2-bromopropylene and deutero-2-bromopropylenes rather than the 3-bromo isomers. The preparation of 3-bromopentadeuteropropene by the allylic bromination of hexadeuteropropene is described. Bromotrichloromethane and 1,3-butadiene gave, under homolytic conditions, trans-5,5,5-trichloro-1-bromo-2-pentene, which was debrominated to a mixture of 5,5,5-trichloropentenes. The latter was then dechlorinated to 1-pentene, which contained some 2-pentenes. Hexadeuterobutadiene reacted similarly to give the corresponding deuterated compounds.