| Stereochemistry of the coupling step in photo-S_(RN) 1 reaction |
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| 基金项目： | Project supported by the National Natural Science Foundation of China. |
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| 摘 要： | 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)~-.
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Stereochemistry of the coupling step in photo-SRN 1 reaction |
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| Bi-Qi Wu,Fan-Wen Zeng,Yong Zhao,Guo-Sheng Wu. Stereochemistry of the coupling step in photo-SRN 1 reaction[J]. Chinese Journal of Chemistry, 1992, 10(3): 253-261. DOI: 10.1002/cjoc.19920100310 |
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| Authors: | Bi-Qi Wu Fan-Wen Zeng Yong Zhao Guo-Sheng Wu |
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| Abstract: | The photo-SRN 1 reaction of (+)-camphor and aryl halides was investigated in order to estimate the stereochemistry of the coupling step of aryl radicals with a nucleophile. The ratio of endo to exo 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 aryl radical. In addition, fragmentation of (ArX)? was found to be related to the energy of SOMO of (ArX)?. |
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