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Volumn , Issue 3, 2000, Pages 189-190

Can α-sultone exist as a chemical species? First experimental implication for intermediacy of α-sultone

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; SULFUR DERIVATIVE; SULTONE;

EID: 0034615090     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909094k     Document Type: Article
Times cited : (11)

References (27)
  • 2
    • 33947458804 scopus 로고
    • For reviews, see: A. Mustafa, Chem. Rev., 1954, 55, 195; D. W. Roberts and D. L. Williams, Tetrahedron, 1987, 43, 1027.
    • (1954) Chem. Rev. , vol.55 , pp. 195
    • Mustafa, A.1
  • 3
    • 0001411520 scopus 로고
    • For reviews, see: A. Mustafa, Chem. Rev., 1954, 55, 195; D. W. Roberts and D. L. Williams, Tetrahedron, 1987, 43, 1027.
    • (1987) Tetrahedron , vol.43 , pp. 1027
    • Roberts, D.W.1    Williams, D.L.2
  • 4
    • 0009683001 scopus 로고
    • J. L. Boyer, B. Gilot and J.-P. Canselier, Phosphorus Sulfur, 1984, 20, 259; W. A. Thaler and C. duBreuil, J. Polym. Sci., 1984, 22, 3905; H. Cerfontain, J. B. Kramer, R. M. Schonk and B. H. Bakker, Recl. Trav. Chim. Pays-Bas, 1995, 114, 410 and references cited therein.
    • (1984) Phosphorus Sulfur , vol.20 , pp. 259
    • Boyer, J.L.1    Gilot, B.2    Canselier, J.-P.3
  • 5
    • 0021585331 scopus 로고
    • J. L. Boyer, B. Gilot and J.-P. Canselier, Phosphorus Sulfur, 1984, 20, 259; W. A. Thaler and C. duBreuil, J. Polym. Sci., 1984, 22, 3905; H. Cerfontain, J. B. Kramer, R. M. Schonk and B. H. Bakker, Recl. Trav. Chim. Pays-Bas, 1995, 114, 410 and references cited therein.
    • (1984) J. Polym. Sci. , vol.22 , pp. 3905
    • Thaler, W.A.1    DuBreuil, C.2
  • 6
    • 0343834903 scopus 로고
    • and references cited therein
    • J. L. Boyer, B. Gilot and J.-P. Canselier, Phosphorus Sulfur, 1984, 20, 259; W. A. Thaler and C. duBreuil, J. Polym. Sci., 1984, 22, 3905; H. Cerfontain, J. B. Kramer, R. M. Schonk and B. H. Bakker, Recl. Trav. Chim. Pays-Bas, 1995, 114, 410 and references cited therein.
    • (1995) Recl. Trav. Chim. Pays-Bas , vol.114 , pp. 410
    • Cerfontain, H.1    Kramer, J.B.2    Schonk, R.M.3    Bakker, B.H.4
  • 7
    • 37049113686 scopus 로고
    • D. W. Roberts, D. L. Williams and D. Bethell, J. Chem. Soc., Perkin Trans. 2, 1985, 389; D. W. Roberts, P. S. Jackson, C. D. Saul and C. J. Clemett, Tetrahedron Lett., 1987, 28, 3383; J. Haller, B. R. Beno and K. N. Houk, J. Am. Chem. Soc., 1998, 120, 6468; J. O. Morley, D. W. Roberts and S. P. Watson, J. Chem. Soc., Perkin Trans. 2, 1999, 1819.
    • (1985) J. Chem. Soc., Perkin Trans. 2 , pp. 389
    • Roberts, D.W.1    Williams, D.L.2    Bethell, D.3
  • 8
    • 0343399147 scopus 로고
    • D. W. Roberts, D. L. Williams and D. Bethell, J. Chem. Soc., Perkin Trans. 2, 1985, 389; D. W. Roberts, P. S. Jackson, C. D. Saul and C. J. Clemett, Tetrahedron Lett., 1987, 28, 3383; J. Haller, B. R. Beno and K. N. Houk, J. Am. Chem. Soc., 1998, 120, 6468; J. O. Morley, D. W. Roberts and S. P. Watson, J. Chem. Soc., Perkin Trans. 2, 1999, 1819.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3383
    • Roberts, D.W.1    Jackson, P.S.2    Saul, C.D.3    Clemett, C.J.4
  • 9
    • 0032496940 scopus 로고    scopus 로고
    • D. W. Roberts, D. L. Williams and D. Bethell, J. Chem. Soc., Perkin Trans. 2, 1985, 389; D. W. Roberts, P. S. Jackson, C. D. Saul and C. J. Clemett, Tetrahedron Lett., 1987, 28, 3383; J. Haller, B. R. Beno and K. N. Houk, J. Am. Chem. Soc., 1998, 120, 6468; J. O. Morley, D. W. Roberts and S. P. Watson, J. Chem. Soc., Perkin Trans. 2, 1999, 1819.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6468
    • Haller, J.1    Beno, B.R.2    Houk, K.N.3
  • 10
    • 84961985406 scopus 로고    scopus 로고
    • D. W. Roberts, D. L. Williams and D. Bethell, J. Chem. Soc., Perkin Trans. 2, 1985, 389; D. W. Roberts, P. S. Jackson, C. D. Saul and C. J. Clemett, Tetrahedron Lett., 1987, 28, 3383; J. Haller, B. R. Beno and K. N. Houk, J. Am. Chem. Soc., 1998, 120, 6468; J. O. Morley, D. W. Roberts and S. P. Watson, J. Chem. Soc., Perkin Trans. 2, 1999, 1819.
    • (1999) J. Chem. Soc., Perkin Trans. 2 , pp. 1819
    • Morley, J.O.1    Roberts, D.W.2    Watson, S.P.3
  • 11
    • 0000689603 scopus 로고    scopus 로고
    • ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford
    • R. W. Murray and M. Singh, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 1A, p. 429; W. Adam and S. Weinkötz, Chem. Commun., 1996, 177; R. Huisgen, G. Mloston, K. Polborn and F. Palacios-Gambra, Liebigs Ann./Rec., 1997, 187; A. Kirschfeld, S. Muthusamy and W. Sander, Angew. Chem., Int. Ed. Engl., 1994, 33, 2212; A. Ishii, T. Akazawa, T. Maruta, J. Nakayama, M. Hoshino and M. Shiro, Angew. Chem., Int. Ed. Engl., 1994, 33, 777.
    • (1996) Comprehensive Heterocyclic Chemistry Ii , vol.1 A , pp. 429
    • Murray, R.W.1    Singh, M.2
  • 12
    • 0002877941 scopus 로고    scopus 로고
    • R. W. Murray and M. Singh, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 1A, p. 429; W. Adam and S. Weinkötz, Chem. Commun., 1996, 177; R. Huisgen, G. Mloston, K. Polborn and F. Palacios-Gambra, Liebigs Ann./Rec., 1997, 187; A. Kirschfeld, S. Muthusamy and W. Sander, Angew. Chem., Int. Ed. Engl., 1994, 33, 2212; A. Ishii, T. Akazawa, T. Maruta, J. Nakayama, M. Hoshino and M. Shiro, Angew. Chem., Int. Ed. Engl., 1994, 33, 777.
    • (1996) Chem. Commun. , pp. 177
    • Adam, W.1    Weinkötz, S.2
  • 13
    • 0344756818 scopus 로고    scopus 로고
    • R. W. Murray and M. Singh, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 1A, p. 429; W. Adam and S. Weinkötz, Chem. Commun., 1996, 177; R. Huisgen, G. Mloston, K. Polborn and F. Palacios-Gambra, Liebigs Ann./Rec., 1997, 187; A. Kirschfeld, S. Muthusamy and W. Sander, Angew. Chem., Int. Ed. Engl., 1994, 33, 2212; A. Ishii, T. Akazawa, T. Maruta, J. Nakayama, M. Hoshino and M. Shiro, Angew. Chem., Int. Ed. Engl., 1994, 33, 777.
    • (1997) Liebigs Ann./Rec. , pp. 187
    • Huisgen, R.1    Mloston, G.2    Polborn, K.3    Palacios-Gambra, F.4
  • 14
    • 33748231395 scopus 로고
    • R. W. Murray and M. Singh, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 1A, p. 429; W. Adam and S. Weinkötz, Chem. Commun., 1996, 177; R. Huisgen, G. Mloston, K. Polborn and F. Palacios-Gambra, Liebigs Ann./Rec., 1997, 187; A. Kirschfeld, S. Muthusamy and W. Sander, Angew. Chem., Int. Ed. Engl., 1994, 33, 2212; A. Ishii, T. Akazawa, T. Maruta, J. Nakayama, M. Hoshino and M. Shiro, Angew. Chem., Int. Ed. Engl., 1994, 33, 777.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 2212
    • Kirschfeld, A.1    Muthusamy, S.2    Sander, W.3
  • 15
    • 33749984095 scopus 로고
    • R. W. Murray and M. Singh, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 1A, p. 429; W. Adam and S. Weinkötz, Chem. Commun., 1996, 177; R. Huisgen, G. Mloston, K. Polborn and F. Palacios-Gambra, Liebigs Ann./Rec., 1997, 187; A. Kirschfeld, S. Muthusamy and W. Sander, Angew. Chem., Int. Ed. Engl., 1994, 33, 2212; A. Ishii, T. Akazawa, T. Maruta, J. Nakayama, M. Hoshino and M. Shiro, Angew. Chem., Int. Ed. Engl., 1994, 33, 777.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 777
    • Ishii, A.1    Akazawa, T.2    Maruta, T.3    Nakayama, J.4    Hoshino, M.5    Shiro, M.6
  • 16
    • 0030830478 scopus 로고    scopus 로고
    • Y. Morimoto and C. Yokoe, Tetrahedron Lett., 1997, 38, 8981; Y. Morimoto, C. Yokoe, H. Kurihara and T. Kinoshita, Tetrahedron, 1998, 54, 12197.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8981
    • Morimoto, Y.1    Yokoe, C.2
  • 19
    • 84981826057 scopus 로고
    • For reviews, see: G. Opitz, Angew. Chem., Int. Ed. Engl., 1967, 6, 107; N. H. Fischer, Synthesis, 1970, 393; J. F. King, Acc. Chem. Res., 1975, 8, 10.
    • (1967) Angew. Chem., Int. Ed. Engl. , vol.6 , pp. 107
    • Opitz, G.1
  • 20
    • 0038444219 scopus 로고
    • For reviews, see: G. Opitz, Angew. Chem., Int. Ed. Engl., 1967, 6, 107; N. H. Fischer, Synthesis, 1970, 393; J. F. King, Acc. Chem. Res., 1975, 8, 10.
    • (1970) Synthesis , pp. 393
    • Fischer, N.H.1
  • 21
    • 0003161990 scopus 로고
    • For reviews, see: G. Opitz, Angew. Chem., Int. Ed. Engl., 1967, 6, 107; N. H. Fischer, Synthesis, 1970, 393; J. F. King, Acc. Chem. Res., 1975, 8, 10.
    • (1975) Acc. Chem. Res. , vol.8 , pp. 10
    • King, J.F.1
  • 22
    • 0000912934 scopus 로고
    • For the formation of the thietane 1,1-dioxides from sulfenes and nucleophilic olefins such as enamines and enol ethers, see: (a) W. E. Truce and J. R. Norell, J. Am. Chem. Soc., 1963, 85, 3231;
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 3231
    • Truce, W.E.1    Norell, J.R.2
  • 24
    • 0032495782 scopus 로고    scopus 로고
    • The readiness for intramolecular cyclization of carbanions to three-membered rings has been theoretically suggested as a proximity effect. See: S. Gronert, K. Azizian and M. A. Friedman, J. Am. Chem. Soc., 1998, 120, 3220. During the deoxygenations of tertiary amine oxides with carbon disulfide, the formation of three-membered ring intermediates from the analogous adduct such as C has been invoked. See: T. Yoshimura, K. Asada and S. Oae, Bull. Chem. Soc. Jpn., 1982, 55, 3000.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3220
    • Gronert, S.1    Azizian, K.2    Friedman, M.A.3
  • 25
    • 0041394895 scopus 로고
    • The readiness for intramolecular cyclization of carbanions to three-membered rings has been theoretically suggested as a proximity effect. See: S. Gronert, K. Azizian and M. A. Friedman, J. Am. Chem. Soc., 1998, 120, 3220. During the deoxygenations of tertiary amine oxides with carbon disulfide, the formation of three-membered ring intermediates from the analogous adduct such as C has been invoked. See: T. Yoshimura, K. Asada and S. Oae, Bull. Chem. Soc. Jpn., 1982, 55, 3000.
    • (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 3000
    • Yoshimura, T.1    Asada, K.2    Oae, S.3
  • 26
    • 0000862318 scopus 로고
    • ed. B. S. Thyagarajan, Interscience, New York
    • L. A. Paquette, in Mechanism of Molecular Migrations, ed. B. S. Thyagarajan, Interscience, New York, 1968, vol. I, p. 121; L. A. Paquette, Acc. Chem. Res., 1968, 1, 209.
    • (1968) Mechanism of Molecular Migrations , vol.1 , pp. 121
    • Paquette, L.A.1
  • 27
    • 0001533568 scopus 로고
    • L. A. Paquette, in Mechanism of Molecular Migrations, ed. B. S. Thyagarajan, Interscience, New York, 1968, vol. I, p. 121; L. A. Paquette, Acc. Chem. Res., 1968, 1, 209.
    • (1968) Acc. Chem. Res. , vol.1 , pp. 209
    • Paquette, L.A.1


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