Synthesis of alcohols, ethers, and amides via mercuration

The addition of chlorine and bromine to olefins is a very general reaction. 

Substantial amounts of syn addition have been observed for cis-1-phenylpropene (27-80% syn addition), trans-l-phenylpropene (17-29% syn addition), and ds-stilbene (up to 90% syn addition in polar solvents). A common feature 

The intermediate has carbonium character at the phenyl-substituted carbon. The effect of this diminished bridging is to increase the rate of rotation around the central C-C bond. If such rotation takes place, anti stereospecificity is, of course, lost. 

Chlorination shows relatively less tendency to give anti addition products than does bromination. Although chlorination of aliphatic olefins gives largely anti addition, syn addition is often dominant for phenyl-substituted olefins  

Chlorination can be accompanied by reactions characteristic of carbonium-ion intermediates. Branched olefins can give products that are the result of elimination of a proton from a cationic intermediate  

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Scheme 3.4. Synthesis of Alcohols, Ethers, and Amides via Mercuration...

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