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Paper | Regular issue | Vol 43, No. 5, 1996, pp.959-968
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7367
Regio- and Stereochemical Control in the Photodimerization of Methyl 3-(2-Furyl)acrylate

Maurizio D'Auria

*Dipartimento di Chimica, Università della Basilicata, Via N. Sauro 85, 85100 Potenza, Italy


The photochemical dimerization of methyl 3-(2-furyl)acrylate in acetonitrile in the presence of benzophenone as triplet sensitizer was reinvestigated in order to understand regio- and stereochemical control. Hplc purification of the dimers and 1H-nmr data allow to correct a wrong structural assignment for a dimer found in the reaction. Regiochemical control can be understood on the of frontier orbitals interaction. Stereochemical control depends on the stability of the dimers. All these data were obtained by the use of the AM1 semiempirical method.