V.V.Veduta, L.D.Patsenker*, V.F.Anikin
Received July 5, 1998
Structural factors influencing
the stereochemical selectivity of electrophilic bromine addition to acenaphthylene
and model cyclic and acyclic alkenes have been revealed using semi-empirical
quantum chemical calculations. The non-stereospecific addition to acenaphthylene
has been shown to be described adequately by the reaction path via the
open carbenium bromide intermediate. The cycloalkene size diminution results
in a lowered probability of the cyclic cationic intermediate and of the
stereoselectivity of bromination.