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Synlett 1997; 1997(11): 1265-1268
DOI: 10.1055/s-1997-1554
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Ab initio MO Calculations for Isomerization Mechanism of the 3-Oxocyclopentylmethyl Radical to the 3-Oxocyclohexyl Radical

Ilhyong Ryu1 , Hiroshi Fukushima, Tohru Okuda, Kazutoshi Matsu, Nobuaki Kambe, Noboru Sonoda2 , Mitsuo Komatsu
  • 1Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565, Japan, Fax: +81 6 879 7402; E-mail: ryu@chem.eng.osaka-u.ac.jp
  • 2Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565, Japan, Fax: +81 6 879 7402
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Publication Date:
31 December 2000 (online)

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An ab initio MO calculation study concerning the isomerization mechanism of the 3-oxocyclopentylmethyl radical to the 3-oxocyclohexyl radical was carried out. Comparison of the energies between the reverting process, leading to the ring-opened 5-hexenoyl radical (path a) and the isomerization pathway (path b) resulted in an energetic preference for the latter. The cyclopropoxy radical intermediate was not rigorously supported at the levels of calculations examined.

ab initio MO calculations - isomerization - 3-oxocyclopentylmethyl radical - 3-oxocyclohexyl radical - acyl radical cyclization