Transannular electrophilic addition reaction of halogens to face-to-face (juxtaposed) double bonded strained alkenes were theoretically investigated. General rules that allow us to stipulate the factors that direct the main steps of the energy hypersurface of reactions as well as the products were established. Direction of the reaction flow is determined by direction of intramolecular skeletal isomerisation of cyclic-bridged halogenium cation and isomerisation takes place to create a more stable skeletal structure. Stability of resultant skeletal structure is determined by the number of s bonds between isolated double bonds of the alkene and bonding-type of double bonds (N-and U-type). When the number of s bonds between double bonds of the alkene is three (m = 3), the reaction takes place to predominantly give an N-type product, and when four (m = 4), N-and U-type products are formed. Structure and stability of cation intermediates (bridged, N-and U-type cations) of electrophilic addition reaction of homohipostrofen molecule, whose double bonds were linked by three s bonds, with bromine were investigated by DFT methods in detail. Also the addition reaction of endo, endo-tetracyclo[220.127.116.11(3,6).0(2,7)] tetradeca-4,9-dien molecule, whose double bonds were linked by four s bonds, with bromine were investigated by quantum chemistry.