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Volumn 62, Issue 15, 1997, Pages 4949-4954

Synthesis of Hydroxy(or Hydroperoxy)-Substituted 1,2,4-Trioxacycloalkanes by the Ozonolysis of Unsaturated Hydroperoxy Acetals

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CYCLOALKANE DERIVATIVE; METHANOL;

EID: 0030872274     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970555l     Document Type: Article
Times cited : (34)

References (30)
  • 6
    • 0031023513 scopus 로고    scopus 로고
    • (c) Bloodworth, A. J.; Hagen, T.; Johnson, K. A.; LeNoir, I.; Mousay, C. Tetrahedron Lett. 1997, 38, 635. For the synthesis of 1,2,4-trioxanes, see: (a) Bunnelle, W. H.; Isbell, T. A.; Barnes, C. L.; Quails, S. J. Am. Chem. Soc. 1991, 113, 8168. (b) Bloodworh, A. J.; Tallant, N. A. J. Chem. Soc., Chem. Commun. 1992, 428. (c) Fujisaka, T.; Miura, M.; Nojima, M.; Kusabayashi, S. J. Chem. Soc., Perkin Trans, 1 1989, 1031. (d) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211 and the references therein. For the synthesis of trioxepane, see: (a) Adam, W.; Duran, N. J. Chem. Soc., Chem. Commun. 1972, 798.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 635
    • Bloodworth, A.J.1    Hagen, T.2    Johnson, K.A.3    LeNoir, I.4    Mousay, C.5
  • 7
    • 0001467049 scopus 로고
    • (c) Bloodworth, A. J.; Hagen, T.; Johnson, K. A.; LeNoir, I.; Mousay, C. Tetrahedron Lett. 1997, 38, 635. For the synthesis of 1,2,4-trioxanes, see: (a) Bunnelle, W. H.; Isbell, T. A.; Barnes, C. L.; Quails, S. J. Am. Chem. Soc. 1991, 113, 8168. (b) Bloodworh, A. J.; Tallant, N. A. J. Chem. Soc., Chem. Commun. 1992, 428. (c) Fujisaka, T.; Miura, M.; Nojima, M.; Kusabayashi, S. J. Chem. Soc., Perkin Trans, 1 1989, 1031. (d) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211 and the references therein. For the synthesis of trioxepane, see: (a) Adam, W.; Duran, N. J. Chem. Soc., Chem. Commun. 1972, 798.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8168
    • Bunnelle, W.H.1    Isbell, T.A.2    Barnes, C.L.3    Quails, S.4
  • 8
    • 0026578601 scopus 로고
    • (c) Bloodworth, A. J.; Hagen, T.; Johnson, K. A.; LeNoir, I.; Mousay, C. Tetrahedron Lett. 1997, 38, 635. For the synthesis of 1,2,4-trioxanes, see: (a) Bunnelle, W. H.; Isbell, T. A.; Barnes, C. L.; Quails, S. J. Am. Chem. Soc. 1991, 113, 8168. (b) Bloodworh, A. J.; Tallant, N. A. J. Chem. Soc., Chem. Commun. 1992, 428. (c) Fujisaka, T.; Miura, M.; Nojima, M.; Kusabayashi, S. J. Chem. Soc., Perkin Trans, 1 1989, 1031. (d) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211 and the references therein. For the synthesis of trioxepane, see: (a) Adam, W.; Duran, N. J. Chem. Soc., Chem. Commun. 1972, 798.
    • (1992) J. Chem. Soc., Chem. Commun. , pp. 428
    • Bloodworh, A.J.1    Tallant, N.A.2
  • 9
    • 3042590245 scopus 로고
    • (c) Bloodworth, A. J.; Hagen, T.; Johnson, K. A.; LeNoir, I.; Mousay, C. Tetrahedron Lett. 1997, 38, 635. For the synthesis of 1,2,4-trioxanes, see: (a) Bunnelle, W. H.; Isbell, T. A.; Barnes, C. L.; Quails, S. J. Am. Chem. Soc. 1991, 113, 8168. (b) Bloodworh, A. J.; Tallant, N. A. J. Chem. Soc., Chem. Commun. 1992, 428. (c) Fujisaka, T.; Miura, M.; Nojima, M.; Kusabayashi, S. J. Chem. Soc., Perkin Trans, 1 1989, 1031. (d) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211 and the references therein. For the synthesis of trioxepane, see: (a) Adam, W.; Duran, N. J. Chem. Soc., Chem. Commun. 1972, 798.
    • (1989) J. Chem. Soc., Perkin Trans, 1 , pp. 1031
    • Fujisaka, T.1    Miura, M.2    Nojima, M.3    Kusabayashi, S.4
  • 10
    • 0001985625 scopus 로고
    • (c) Bloodworth, A. J.; Hagen, T.; Johnson, K. A.; LeNoir, I.; Mousay, C. Tetrahedron Lett. 1997, 38, 635. For the synthesis of 1,2,4-trioxanes, see: (a) Bunnelle, W. H.; Isbell, T. A.; Barnes, C. L.; Quails, S. J. Am. Chem. Soc. 1991, 113, 8168. (b) Bloodworh, A. J.; Tallant, N. A. J. Chem. Soc., Chem. Commun. 1992, 428. (c) Fujisaka, T.; Miura, M.; Nojima, M.; Kusabayashi, S. J. Chem. Soc., Perkin Trans, 1 1989, 1031. (d) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211 and the references therein. For the synthesis of trioxepane, see: (a) Adam, W.; Duran, N. J. Chem. Soc., Chem. Commun. 1972, 798.
    • (1994) Acc. Chem. Res. , vol.27 , pp. 211
    • Zhou, W.-S.1    Xu, X.-X.2
  • 11
    • 37049142744 scopus 로고
    • (c) Bloodworth, A. J.; Hagen, T.; Johnson, K. A.; LeNoir, I.; Mousay, C. Tetrahedron Lett. 1997, 38, 635. For the synthesis of 1,2,4-trioxanes, see: (a) Bunnelle, W. H.; Isbell, T. A.; Barnes, C. L.; Quails, S. J. Am. Chem. Soc. 1991, 113, 8168. (b) Bloodworh, A. J.; Tallant, N. A. J. Chem. Soc., Chem. Commun. 1992, 428. (c) Fujisaka, T.; Miura, M.; Nojima, M.; Kusabayashi, S. J. Chem. Soc., Perkin Trans, 1 1989, 1031. (d) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211 and the references therein. For the synthesis of trioxepane, see: (a) Adam, W.; Duran, N. J. Chem. Soc., Chem. Commun. 1972, 798.
    • (1972) J. Chem. Soc., Chem. Commun. , pp. 798
    • Adam, W.1    Duran, N.2
  • 26
    • 85033128536 scopus 로고    scopus 로고
    • Unpublished result
    • Ozonolysis of β-methoxystyrene in trifluoroethanol - ether gives a complex mixture of products including 3,6-diphenyl-1,2,4,5-tetraoxane and benzaldehyde; no evidence is obtained for the formation of the products derived from capture of benzaldehyde oxide by trifluoroethanol. Ushigoe, Y.; Nojima, M. Unpublished result.
    • Ushigoe, Y.1    Nojima, M.2


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