Why the presence of a phenyl group causes loss of stereospecificity in this alkene bromination?

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Robert · Accepted Answer

Solution to TTs230912_41152_1
Let us see how bromination of alkenes takes place.  
A cyclic bromonium ion is formed first, followed by the nucleophilic 
attack by the residual bromide ion. Highly sterospecific ANTI addition 
takes place because of cyclic bromonium  ion intermediate.

Why the presence of a phenyl group causes loss of stereospecificity in this alkene bromination?

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