The early stages of the [3+2]-photocycloaddition of 1,4-dicyano-6-methylnaphthalene (6) with styrene (7) were investigated by UV–visible absorption and 1H NMR spectroscopy. An intermediate species was detected and characterized as 8-methyl-2-phenyl-1,2,2a,8-tetrahydroacenaphthylene-2a,5-dicarbonitrile (9). Computational studies explained the regioselective [3+2]-photocycloaddition at the 4,5-position of 6 to form zwitterion 8, and subsequent thermal transformation to form 9.
Research on Chemical Intermediates – Springer Journals
Published: Jul 8, 2012
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