Stereochemistry of the coupling step in photo‐S RN  1 reaction | Zendy

Wu BiQi | Zendy; Zeng FanWen | Zendy; Zhao Yong | Zendy; Wu GuoSheng | Zendy

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Stereochemistry of the coupling step in photo‐S RN 1 reaction

Author(s) -

Wu BiQi,

Zeng FanWen,

Zhao Yong,

Wu GuoSheng

Publication year - 1992

Publication title -

chinese journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.28

H-Index - 41

eISSN - 1614-7065

pISSN - 1001-604X

DOI - 10.1002/cjoc.19920100310

Subject(s) - chemistry , mndo , aryl , radical , nucleophile , aryl radical , fragmentation (computing) , halide , ion , computational chemistry , photochemistry , coupling reaction , molecular orbital , stereochemistry , medicinal chemistry , molecule , organic chemistry , alkyl , computer science , operating system , catalysis

The photo‐S RN 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 1 H 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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