메뉴 건너뛰기




Volumn 130, Issue 4, 2008, Pages 1197-1204

Concerning the reactivity of dioxiranes. Observations from experiments and theory

Author keywords

[No Author keywords available]

Indexed keywords

CINNAMONITRILES; DIMETHYLDIOXIRANE; DIOXIRANES;

EID: 38849108881     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075068u     Document Type: Article
Times cited : (32)

References (77)
  • 14
    • 38849176397 scopus 로고    scopus 로고
    • IASOC - Ischia Advanced School of Organic Chemistry, VIII Session, Ischia (Italy)
    • September 26-October 1
    • (f) Curci, R. IASOC - Ischia Advanced School of Organic Chemistry, VIII Session, Ischia (Italy); September 26-October 1, 1998; Abstracts, L9.
    • (1998) Abstracts , vol.L9
    • Curci, R.1
  • 16
    • 0004082709 scopus 로고    scopus 로고
    • Patai, S, Ed, Wiley: New York, Chapter 14. See references therein
    • (b) Adam, W.; Zhao, C.-G. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: New York, 2006; Vol. 2, Chapter 14. See references therein.
    • (2006) The Chemistry of Peroxides , vol.2
    • Adam, W.1    Zhao, C.-G.2
  • 20
    • 0004082709 scopus 로고    scopus 로고
    • Patai, S, Ed, Wiley: New York, Chapter 1. See references therein
    • Bach, R. D. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: New York, 2006; Vol. 1, Chapter 1. See references therein.
    • (2006) The Chemistry of Peroxides , vol.1
    • Bach, R.D.1
  • 22
    • 0002131753 scopus 로고
    • Strukul, G, Ed, Kluwer: Dodrecht, The Netherlands, Chapter 3, pp, See references therein
    • 2 as Oxidant; Strukul, G., Ed.; Kluwer: Dodrecht, The Netherlands, 1992; Chapter 3, pp 45-95. See references therein.
    • (1992) 2 as Oxidant , pp. 45-95
    • Curci, R.1    Edwards, J.O.2
  • 39
    • 0001287756 scopus 로고    scopus 로고
    • Bonchio, M; Conte, V.; DiFuria, F.; Modena, G.; Moro, S.; Carofiglio T.; Magno, F.; Pastore, P. Inorg. Chem. 1993, 32, 5797. See also references therein.
    • (d) Bonchio, M; Conte, V.; DiFuria, F.; Modena, G.; Moro, S.; Carofiglio T.; Magno, F.; Pastore, P. Inorg. Chem. 1993, 32, 5797. See also references therein.
  • 41
  • 43
    • 0034981362 scopus 로고    scopus 로고
    • Araki, T.; Kitaoka, H. Chem. Pharm. Bull. 2001, 49, 541. See also references therein.
    • (c) Araki, T.; Kitaoka, H. Chem. Pharm. Bull. 2001, 49, 541. See also references therein.
  • 49
    • 38849191349 scopus 로고    scopus 로고
    • Bach, R. D. In DFG Research Report on Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer, Adam, W., Saha-Möller, C. R., Eds.; Wiley-VCH: Weinheim, 2000; p 569.
    • (c) Bach, R. D. In DFG Research Report on Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer, Adam, W., Saha-Möller, C. R., Eds.; Wiley-VCH: Weinheim, 2000; p 569.
  • 54
    • 0037423178 scopus 로고    scopus 로고
    • (b) J. Org. Chem. 2003, 68, 811;
    • (2003) J. Org. Chem , vol.68 , pp. 811
  • 55
    • 0034731624 scopus 로고    scopus 로고
    • (c) J. Org. Chem. 2000, 65, 8948;
    • (2000) J. Org. Chem , vol.65 , pp. 8948
  • 56
    • 84961983433 scopus 로고    scopus 로고
    • (d) Tetrahedron 1998, 54, 12323;
    • (1998) Tetrahedron , vol.54 , pp. 12323
  • 57
    • 27744486097 scopus 로고    scopus 로고
    • (e) J. Org. Chem. 2005, 70, 9573.
    • (2005) J. Org. Chem , vol.70 , pp. 9573
  • 58
    • 0033553133 scopus 로고    scopus 로고
    • For an excellent discussion about the qualitative use-of Kohn-Sham orbitals to rationalize chemical phenomena, see: Stowasser, R, Hoffmann, R. J. Am. Chem. Soc. 1999, 121, 3414
    • For an excellent discussion about the qualitative use-of Kohn-Sham orbitals to rationalize chemical phenomena, see: Stowasser, R.; Hoffmann, R. J. Am. Chem. Soc. 1999, 121, 3414.
  • 59
    • 38849120933 scopus 로고    scopus 로고
    • It should be mentioned that the energy barriers both from experiments and from computations should diminish markedly on going from gas to condensed phase. For instance, an experimental Ea of 8.0 kcal mol -1 at 25° C (ΔH≠ of 7.4 kcal mol-1) has been measured for the DDO epoxidation of cyclohexene in an acetone solvent (ref 4c, The Ea values of 11.4 and 10.7 kcal mol-1 have been estimated for the DDO epoxidation of cyclohexene in CHCl3 and acetone, respectively, using the COSMO solvent mode [B3LYP/6-311+G(d,p, ref 7, The increased reactivity in polar solvents might be attributed to enhanced polarization of the TS relative to reactants; theoretical solvation studies are consistent with these observations Jenson, C, Liu, J, Houk, K. N, Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982, a systematic study of the effects of solvation and hydrogen bonding
    • 3 and acetone, respectively, using the COSMO solvent mode [B3LYP/6-311+G(d,p)] (ref 7). The increased reactivity in polar solvents might be attributed to enhanced polarization of the TS relative to reactants; theoretical solvation studies are consistent with these observations (Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982); a systematic study of the effects of solvation and hydrogen bonding was also carried out by Gandolfi et al. at the B3LYP/6-31G(d) level (ref 23)
  • 64
    • 38849201318 scopus 로고    scopus 로고
    • This work, DFT computations; values optimized using B3LYP/6-31G(d) data
    • This work, DFT computations; values optimized using B3LYP/6-31G(d) data.
  • 77
    • 38849127052 scopus 로고    scopus 로고
    • Gaussian, Inc, Pittsburgh, PA, For full citation, see Supporting Information
    • Frisch, M. J. et al. Gaussian 03, Revision C. 02; Gaussian, Inc.: Pittsburgh, PA, 2003. For full citation, see Supporting Information.
    • (2003) Gaussian 03, Revision , Issue.C. 02
    • Frisch, M.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.