REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN THE PHOTODIMERIZATION OF METHYL-3-(2-FURYL)ACRYLATE

The photochemical dimerization of methyl 3-(2-furyl)acrylate in aceton itrile in the presence of benzophenone as triplet sensitizer was reinv estigated in order to understand regio-and stereochemical control. Hpl c purification of the dimers and H-1-nmr data allow to correct a wrong structural assignment for a dimer found in the reaction. Regiochemica l control can be understood on the of frontier orbitals interaction. S tereochemical control depends on the stability of the dimers. All thes e data were obtained by the use of the AM1 semiempirical method.