Quantum chemical simulation of the bromine electrophilic addition to acenaphthylene

V.V.Veduta, L.D.Patsenker*, V.F.Anikin

Odessa State University, 2 Dvoryanskaya Str., 270100, Odessa, Ukraine
*Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 Lenin Ave., 310001, Kharkiv, Ukraine

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.

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