A Comparative Study of the Possible EliminationReactions on Compound of 5,6-Difluoro-5,6-dihydrocyclohexa-1,3-diene

The aim of the present research is to predict decomposition reaction product of 5,6-difluoro-5,6-dihydrocyclohexa- 1,3-diene(a) from three possible products, using DFT-B3LYP method. The calculation results showed that 5,6- hydrofluoration elimination reaction is most possible, because the required energy (Ea=35.31kcalmol-1) for this reaction is lower than another possibilities (Ea for elimination of 5,6-difluorine=86.03kcalmol-1, Ea for elimination of 5,6-dihydro=68.26 kcalmol-1). We performed a DFT calculation on dehydrofluorination this compound (scheme 1). Also, the Nucleus Independent Chemical Shift (NICS) values in the center of the ring, NICS(0), NICS(0.5),NICS(1) are computed. The NICS(0.5) value of product is the most negative value and indicating its highest aromaticity.

Keywords:

Elimination , DFT , Ea , NICS