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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) − .