Mechanistic Investigation of the Formation of Isoindole -Oxides in the Electron Transfer-Mediated Oxidative Cyclization of 2'-Alkynylacetophenone Oximes.

This paper describes a joint experiment-theory investigation of the formation and cyclization of 2'-alkynylacetophenone oxime radical cations using photoinduced electron transfer (PET) with DCA as the photosensitizer. Using a combination of experimental H and C nuclear magnetic resonance (NMR) spectra, high-resolution mass spectrometry, and calculated NMR chemical shifts, we identified the products to be isoindole -oxides. The reaction was found to be stereoselective; only one of the two possible stereoisomers is formed under these conditions.