메뉴 건너뛰기




Volumn 122, Issue 17, 2000, Pages 4039-4043

A novel epoxidation reaction of olefins using a combination of chloramine-M, benzaldehyde, and benzyltriethylammonium chloride

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZALDEHYDE; BENZYL DERIVATIVE; CHLORAMINE DERIVATIVE; CYCLOHEXENE DERIVATIVE; TOSYLCHLORAMIDE SODIUM;

EID: 0034600252     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993472q     Document Type: Article
Times cited : (15)

References (41)
  • 1
    • 0000960640 scopus 로고    scopus 로고
    • For excellent reviews on oxaziridines, see: (a) Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703-5742. (b) Davis, F. A.; Reddy, R. T. In Comprehensive Heterocyclic Chemistry II, 1st ed.; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Series Eds.; Pergamon: New York, 1996; Vol. 1A, Padwa, A., Ed.; pp 365-413.
    • (1989) Tetrahedron , vol.45 , pp. 5703-5742
    • Davis, F.A.1    Sheppard, A.C.2
  • 2
    • 0000960640 scopus 로고    scopus 로고
    • Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Series Eds.; Pergamon: New York, Padwa, A., Ed.
    • For excellent reviews on oxaziridines, see: (a) Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703-5742. (b) Davis, F. A.; Reddy, R. T. In Comprehensive Heterocyclic Chemistry II, 1st ed.; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Series Eds.; Pergamon: New York, 1996; Vol. 1A, Padwa, A., Ed.; pp 365-413.
    • (1996) Comprehensive Heterocyclic Chemistry II, 1st Ed. , vol.1 A , pp. 365-413
    • Davis, F.A.1    Reddy, R.T.2
  • 8
    • 33751154457 scopus 로고
    • For recent examples of epoxidation using dioxiranes generated in situ, see: (a) Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887-3889. (b) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Cheung, K.-K. J. Org. Chem. 1998, 63, 9888-9894. (c) Yang, D.; Yip, Y.-C.; Jiao, G.-S.; Wong, M.-K. J. Org. Chem. 1998, 63, 8952-8956. (d) Frohn, M.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 6425-6426. (e) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407.
    • (1995) J. Org. Chem. , vol.60 , pp. 3887-3889
    • Yang, D.1    Wong, M.-K.2    Yip, Y.-C.3
  • 9
    • 0032567328 scopus 로고    scopus 로고
    • For recent examples of epoxidation using dioxiranes generated in situ, see: (a) Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887-3889. (b) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Cheung, K.-K. J. Org. Chem. 1998, 63, 9888-9894. (c) Yang, D.; Yip, Y.-C.; Jiao, G.-S.; Wong, M.-K. J. Org. Chem. 1998, 63, 8952-8956. (d) Frohn, M.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 6425-6426. (e) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407.
    • (1998) J. Org. Chem. , vol.63 , pp. 9888-9894
    • Yang, D.1    Yip, Y.-C.2    Tang, M.-W.3    Wong, M.-K.4    Cheung, K.-K.5
  • 10
    • 0031794268 scopus 로고    scopus 로고
    • For recent examples of epoxidation using dioxiranes generated in situ, see: (a) Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887-3889. (b) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Cheung, K.-K. J. Org. Chem. 1998, 63, 9888-9894. (c) Yang, D.; Yip, Y.-C.; Jiao, G.-S.; Wong, M.-K. J. Org. Chem. 1998, 63, 8952-8956. (d) Frohn, M.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 6425-6426. (e) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407.
    • (1998) J. Org. Chem. , vol.63 , pp. 8952-8956
    • Yang, D.1    Yip, Y.-C.2    Jiao, G.-S.3    Wong, M.-K.4
  • 11
    • 0000225906 scopus 로고    scopus 로고
    • For recent examples of epoxidation using dioxiranes generated in situ, see: (a) Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887-3889. (b) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Cheung, K.-K. J. Org. Chem. 1998, 63, 9888-9894. (c) Yang, D.; Yip, Y.-C.; Jiao, G.-S.; Wong, M.-K. J. Org. Chem. 1998, 63, 8952-8956. (d) Frohn, M.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 6425-6426. (e) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407.
    • (1998) J. Org. Chem. , vol.63 , pp. 6425-6426
    • Frohn, M.1    Wang, Z.-X.2    Shi, Y.3
  • 12
    • 0000225906 scopus 로고    scopus 로고
    • For recent examples of epoxidation using dioxiranes generated in situ, see: (a) Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887-3889. (b) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Cheung, K.-K. J. Org. Chem. 1998, 63, 9888-9894. (c) Yang, D.; Yip, Y.-C.; Jiao, G.-S.; Wong, M.-K. J. Org. Chem. 1998, 63, 8952-8956. (d) Frohn, M.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 6425-6426. (e) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407.
    • (1995) J. Org. Chem. , vol.60 , pp. 1391-1407
    • Denmark, S.E.1    Forbes, D.C.2    Hays, D.S.3    DePue, J.S.4    Wilde, R.G.5
  • 15
  • 18
    • 33947092359 scopus 로고
    • For a review of Chloramine-T and related reagents, see: Campbell, M. M.; Johnson, G. Chem. Rev. 1978, 78, 65-79.
    • (1978) Chem. Rev. , vol.78 , pp. 65-79
    • Campbell, M.M.1    Johnson, G.2
  • 19
    • 0033525675 scopus 로고    scopus 로고
    • Yang, D.; Jiao, G.-S.; Yip, Y.-C.; Wong, M.-K. J. Org. Chem. 1999, 64, 1635-1639. For diastereoselective epoxidation of cyclohexene derivatives using isolated dimethyldioxirane, see: Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841.
    • (1999) J. Org. Chem. , vol.64 , pp. 1635-1639
    • Yang, D.1    Jiao, G.-S.2    Yip, Y.-C.3    Wong, M.-K.4
  • 20
    • 0001451148 scopus 로고    scopus 로고
    • Yang, D.; Jiao, G.-S.; Yip, Y.-C.; Wong, M.-K. J. Org. Chem. 1999, 64, 1635-1639. For diastereoselective epoxidation of cyclohexene derivatives using isolated dimethyldioxirane, see: Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841.
    • (1996) J. Org. Chem. , vol.61 , pp. 1830-1841
    • Murray, R.W.1    Singh, M.2    Williams, B.L.3    Moncrieff, H.M.4
  • 21
    • 0343935185 scopus 로고    scopus 로고
    • The spectra are provided in the Supporting Information
    • The spectra are provided in the Supporting Information.
  • 22
    • 0000774391 scopus 로고
    • For epoxidation of (+)-limonene using perbenzoic acid, see: Newhall, W. F. J. Org. Chem. 1959, 24, 1673.
    • (1959) J. Org. Chem. , vol.24 , pp. 1673
    • Newhall, W.F.1
  • 26
    • 37049128641 scopus 로고
    • The nucleophilicity of N-chlorotoluene-p-sulfonamidate anion was found to be comparable to that of the azide anion. See: Hardy, F. E. J. Chem. Soc. B 1971, 1899-1902.
    • (1971) J. Chem. Soc. B , pp. 1899-1902
    • Hardy, F.E.1
  • 29
    • 0342629117 scopus 로고    scopus 로고
    • note
    • - has been excluded as the epoxidizing agent (vide supra) and no sulfonimine was detected in Figure 2.
  • 31
    • 0342629115 scopus 로고    scopus 로고
    • note
    • - and epoxidation. The former pathway mainly gives back B but the latter provides the epoxide products. As long as the equilibrium between C and D is set up and D is kinetically competent, according to the Curtin-Hammett principle, epoxide products can be formed. Under our in situ reaction conditions, the concentrations of C and D at equilibrium were low, which explains why epoxidation reactions were generally slow.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.