Étude theorique de la chimio-, régio- et stéréosélectivité de l'interaction entre l'[Alpha]-trans-himachalène et le dichlorocarbène par la méthode de la théorie de la fonctionnelle de la densite (DFT) B3LYP/6-311G (d, p)/[ Theoretical study of the chemo-, regio- and stereoselectivity of the interaction between dichlorocarbene and [Alpha]-trans-himachalene using density functional theory (DFT) B3LYP/6-31G (d, p) ]

The reaction between α-trans-himachalene and dichlorocarbene has been studied using density functional theory (DFT) B3LYP/6-311G (d, p). The global electrophilicity and global nucleophilicity indices indicate that α-trans-himachalene behaves as a nucleophile while dichlorocarbene behaves as an electrophile. The majority product obtained by stoichiometric reaction between dichlorocarbene and α-trans-himachalene is (1R, 2S, 4R, 7S)-3,3-dichloro-8-methylene-4,12,12-trimethyltricyclo [5.5.0.02,4] dodecane (referred to here as P1(α)): in this reaction, the attack takes place at the endocyclic double bond at the α side of α-trans-himachalene. Analysis of local electrophilicity and local nucleophilicity indices demonstrates the chemo-, regio- and stereoselectivity of the reaction. Analysis of the potential energy surface shows that this reaction follows an asynchronous concerted mechanism. Calculating the intrinsic reaction coordinate shows that the reaction mechanism can be characterized as "one-step" and "two-stage". Stationary points were characterized by frequency calculations in order to verify that the transition states had one and only one imaginary frequency.