An Account of the Site- and Regio-selectivity in the Reaction of Nitrile Oxides with Substituted p-Benzoquinones by Frontier Molecular Orbital Theory

The 1,3-dipolar cycloaddition reactions of nitrile oxides with substituted p-benzoquinones are discussed in terms of Frontier Molecular Orbital (FMO) theory. The calculation is carried out by ab initio Self Consistent Field (SCF) method with STO-3G basis set. The site- and regio-selectivities in the reactions are correlated with two types of FMO interactions. Some predictions have been confirmed by experimental results.