REGIOSELECTIVE ADDITIONS OF ELECTROPHILES TO OLEFINS REMOTELY PERTURBED. THE CARBONYL GROUP AS A HOMOCONJUGATED ELECTRON DONATING SUBSTITUENT.

Article abstract of DOI:10.1016/S0040-4039(00)87396-7

Electrophiles attack preferentially at the C(5) position of 2-norborn-5-enone and 2-bicyclo<2.2.2>oct-5-enone whereas the C(6) position is preferred for 2-chloronorborn-5-ene-2-carbonitriles and 2-chlorobicyclo<2.2.2>oct-5-ene-2-carbonitriles.