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Volumn 9, Issue 26, 2007, Pages 5569-5572

Model studies of β-scission ring-opening reactions of cyclohexyloxy radicals: Application to thermal rearrangements of dispiro-1,2,4-trioxanes

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; FREE RADICAL;

EID: 38349173914     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702534d     Document Type: Article
Times cited : (18)

References (42)
  • 8
    • 37349090593 scopus 로고    scopus 로고
    • and previous reviews in series
    • (c) Faulkner, D. J. Nat. Prod. Rep. 2000, 1 and previous reviews in series.
    • (2000) Nat. Prod. Rep , pp. 1
    • Faulkner, D.J.1
  • 16
    • 38349158552 scopus 로고    scopus 로고
    • Thermolyses of artemisinin and other polycyclic 1,2,4-trioxanes generally result in extensive fragmentation of the trioxane ring and/or intramolecular H-abstraction processes after the initial O-O bond homolysis. See for example: (a) Luo, X.-D; Yeh, H. J. C.; Brossi, A.; Flippen-Anderson, J. L.; Gilardi, R. Heterocycles 1985, 23, 881.
    • Thermolyses of artemisinin and other polycyclic 1,2,4-trioxanes generally result in extensive fragmentation of the trioxane ring and/or intramolecular H-abstraction processes after the initial O-O bond homolysis. See for example: (a) Luo, X.-D; Yeh, H. J. C.; Brossi, A.; Flippen-Anderson, J. L.; Gilardi, R. Heterocycles 1985, 23, 881.
  • 24
    • 85028579626 scopus 로고
    • Horspool, W. M, Song, P.-S, Eds, CRC Press: London, and references therein
    • Sugimone, H. In Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: London, 1994; pp 1229-1253 and references therein.
    • (1994) Handbook of Organic Photochemistry and Photobiology , pp. 1229-1253
    • Sugimone, H.1
  • 25
    • 34548424858 scopus 로고    scopus 로고
    • Recent examples include: (a) Alonso-Cruz, C. R.; Kennedy, A. R.; Rodriguez, M. S.; Suarez, E. Tetrahedron Lett. 2007, 48, 7207.
    • Recent examples include: (a) Alonso-Cruz, C. R.; Kennedy, A. R.; Rodriguez, M. S.; Suarez, E. Tetrahedron Lett. 2007, 48, 7207.
  • 29
    • 38349085783 scopus 로고    scopus 로고
    • Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford CT, 2004. Calculations used the B3LYP hybrid functional and 6-3IG** basis sets. AU energies include corrections for zero-point energy. See Supporting Information for full details.
    • Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford CT, 2004. Calculations used the B3LYP hybrid functional and 6-3IG** basis sets. AU energies include corrections for zero-point energy. See Supporting Information for full details.
  • 30
    • 21144441508 scopus 로고    scopus 로고
    • Recent theoretical treatments of β-scission in alkoxy radicals: (a) Thiriot, E.; Canneaux, S.; Hénon, E.; Bohr, F. React. Kinet. Catal. Lett. 2005, 85, 123.
    • Recent theoretical treatments of β-scission in alkoxy radicals: (a) Thiriot, E.; Canneaux, S.; Hénon, E.; Bohr, F. React. Kinet. Catal. Lett. 2005, 85, 123.
  • 32
    • 33645275720 scopus 로고    scopus 로고
    • Leblanc, M.; Siri, D.; Marque, S. R. A.; Grimaldi, S.; Bertin, D.; Tordo, P. Int. 3. Quant. Chem. 2006, 106, 676.
    • (c) Leblanc, M.; Siri, D.; Marque, S. R. A.; Grimaldi, S.; Bertin, D.; Tordo, P. Int. 3. Quant. Chem. 2006, 106, 676.
  • 34
    • 38349190819 scopus 로고    scopus 로고
    • Straight-chain forms of products P 8a (E = +2.7 kcal/mol) and P 9(E = -9.0 kcal/mol) are slightly more stable than the initial intermediates shown in Figure 1 but retain the same thermodynamic preference for opening 9.
    • Straight-chain forms of products P 8a (E = +2.7 kcal/mol) and P 9(E = -9.0 kcal/mol) are slightly more stable than the initial intermediates shown in Figure 1 but retain the same thermodynamic preference for opening 9.
  • 35
    • 38349133542 scopus 로고    scopus 로고
    • Preliminary calculations on the analogous OMe-substituted dispiro1,2,4-trioxanes show this interaction is retained in the full systems; thus, this stabilization is not an artefact of our truncated models.
    • Preliminary calculations on the analogous OMe-substituted dispiro1,2,4-trioxanes show this interaction is retained in the full systems; thus, this stabilization is not an artefact of our truncated models.
  • 36
    • 0004032955 scopus 로고
    • Kochi, J. K, Ed, Wiley: New York
    • Nelson, S. F. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2.
    • (1973) Free Radicals , vol.2
    • Nelson, S.F.1
  • 37
    • 0042734789 scopus 로고    scopus 로고
    • For recent examples where the a-effect is highlighted see: a
    • For recent examples where the a-effect is highlighted see: (a) Rauk, A.; Boyd, R. J.; Boyd, S. L.; Henry, D. J.; Radom, L. Can. J. Chem. 2003, 81, 431.
    • (2003) Can. J. Chem , vol.81 , pp. 431
    • Rauk, A.1    Boyd, R.J.2    Boyd, S.L.3    Henry, D.J.4    Radom, L.5
  • 41
    • 38349143267 scopus 로고    scopus 로고
    • Trace quantities of the ring B fragmentation products cyclohexanone and methoxycyclohexanone were also identified by gas chromatography
    • Trace quantities of the ring B fragmentation products cyclohexanone and methoxycyclohexanone were also identified by gas chromatography.
  • 42
    • 38349154325 scopus 로고    scopus 로고
    • Sheldrick, G. M. SHELXTL PC vers. 5.1, Brucker AXS: Madison, WI, 1997
    • Sheldrick, G. M. SHELXTL PC (vers. 5.1); Brucker AXS: Madison, WI, 1997.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.