The cyclic bromonium ion is strongly electrophilic. The ring
strain and the positive charge on the bromine atom can be relieved by
attack of a nucleophile on a carbon of the cyclic bromonium ion,
resulting in ring opening. This is an SN2 reaction on the
carbon, with concerted C-O bond formation and C-Br bond cleavage.
This take place by nucleophilic attack of water on the backside of the
C-Br bond, resulting in inversion of stereochemistry and formation of
the trans addition product.
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Intermediate:
A cyclic bromonium ion
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