Allyl chloride hydrobromination

Mixtures of isomeric allylic chlorides are formed when 1,1-disubstituted allenes react with HC1.1,3-Disubstituted allenes yield products of both central and terminal carbon attacks. In contrast, selective transformations occur with HBr. The gas-phase, photocatalytic addition of HBr gives selectively vinylic bromides129 [Eq. (6.20)], while hydrobromination in solution phase yields allylic bromides130 [Eq. (6.21)] ... 

The hydrobromination of a number of halogenated alkenes has been examined. Allyl bromide reacts with HBr in the absence of peroxides, or upon addition of antioxidants121 or FeCb,61 or in acetic acid,122 to produce primarily 1,2-dibromopropane (equation 74). Allyl chloride behaves similarly.123... 

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