Theoretical investigation of the mechanism, chemo- and stereospecifity in the epoxidation reaction of limonene with meta-chloroperoxybenzoic acid (m-CPBA)

The epoxidation of limonene 1 with m-CPBA has been examined within the MEDT at the B3LYP/6-311(d,p) computational level. The chemo- and stereoisomeric reaction paths involving the two C=C double bonds of limonene have been scrutinized. DFT computations account for the high chemospecifity involving the C 1 =C 2 double bond and the stereospecifity, in complete conformity with the experimental results. An ELF analysis of the epoxidation shows the formation of the epoxide ring taking place of the two new C-O single bonds is somewhat asynchronous.