An AM1 and DFT-AM1 computational study of methyl phenylpropiolate addition to 1-phenyl-3,4-dimethylphosphole

The transition state structures for the addition of maleic acid anhydride and methyl phenylpropiolate to 1-phenyl-3,4-dimethylphosphole were generated with the AM1 semiempirical method. The competitive transition state structures for 1,5-phenyl rearrangement in 1-phenyl-3,4-dimethylphosphole was also optimized with AM1. The energies were evaluated with the SVWN and Becke3LYP DFT methods using a 6-31G(d) basis set. The reaction outcome based on the evaluated energies were discussed and compared with experimental observations.