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The photo-S_(RN) 1 reaction of (+)-camphor and aryl halides was investigated in order toestimate the stereochemistry of the coupling step of aryl radicals with a nucleophile. The ratio of endo toexo products determined by ~1H NMR and CD spectra was found to be 99:1. MNDO calculationsof the orbital parameters showed a favorable one-sided overlap of the enolate ion with the SOMO of arylradical. In addition, fragmentation of (ArX)~- was found to be related to the energy of SOMO of(ArX)~-.
The photo-S_ (RN) 1 reaction of (+) - camphor and aryl halides was investigated in order totimate the stereochemistry of the coupling step of aryl radicals with a nucleophile. The ratio of endo toexo products determined by ~ 1H NMR and CD spectra was found to be 99: 1. MNDO calculations of the orbital parameters showed a favorable one-sided overlap of the enolate ion with the SOMO of arylradical. In addition, fragmentation of (ArX) ~ - was found to be related to the energy of SOMO of (ArX) ~ -.