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Volumn 125, Issue 26, 2003, Pages 7754-7755

The reaction of thio acids with azides: A new mechanism and new synthetic applications

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; THIOACID;

EID: 0038788894     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0294919     Document Type: Article
Times cited : (322)

References (36)
  • 7
    • 0037746180 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details of preparation and characterization.
  • 9
    • 0035961527 scopus 로고    scopus 로고
    • This proposal also accounts for the remarkable observations described in refs 1-3 as well as those in: (a) Marcaurelle, L. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2001, 123, 1587. (b) Elofsson, M.; Salvador, L. A.; Kihlberg, J. Tetrahedron 1997, 53, 369. (c) Chou, S.-S. P.; Chow, T. J.; Hsu, C.-H.; Yang, C.; Long, S.-H.; Lin, C.-D. J. Chem. Soc., Perkin Trans. 1 1997, 1691. (d) McKervey, M. A.; Sullivan, B. O.; Myers, P. L.; Green, R. H. J. Chem. Soc., Chem. Commun. 1993, 94. See also: Paulsen, H.; Bielfeldt, T.; Peters, S.; Bock, K. Liebigs Ann. Chem. 1994, 369.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1587
    • Marcaurelle, L.A.1    Bertozzi, C.R.2
  • 10
    • 0031060570 scopus 로고    scopus 로고
    • This proposal also accounts for the remarkable observations described in refs 1-3 as well as those in: (a) Marcaurelle, L. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2001, 123, 1587. (b) Elofsson, M.; Salvador, L. A.; Kihlberg, J. Tetrahedron 1997, 53, 369. (c) Chou, S.-S. P.; Chow, T. J.; Hsu, C.-H.; Yang, C.; Long, S.-H.; Lin, C.-D. J. Chem. Soc., Perkin Trans. 1 1997, 1691. (d) McKervey, M. A.; Sullivan, B. O.; Myers, P. L.; Green, R. H. J. Chem. Soc., Chem. Commun. 1993, 94. See also: Paulsen, H.; Bielfeldt, T.; Peters, S.; Bock, K. Liebigs Ann. Chem. 1994, 369.
    • (1997) Tetrahedron , vol.53 , pp. 369
    • Elofsson, M.1    Salvador, L.A.2    Kihlberg, J.3
  • 11
    • 33748670708 scopus 로고    scopus 로고
    • This proposal also accounts for the remarkable observations described in refs 1-3 as well as those in: (a) Marcaurelle, L. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2001, 123, 1587. (b) Elofsson, M.; Salvador, L. A.; Kihlberg, J. Tetrahedron 1997, 53, 369. (c) Chou, S.-S. P.; Chow, T. J.; Hsu, C.-H.; Yang, C.; Long, S.-H.; Lin, C.-D. J. Chem. Soc., Perkin Trans. 1 1997, 1691. (d) McKervey, M. A.; Sullivan, B. O.; Myers, P. L.; Green, R. H. J. Chem. Soc., Chem. Commun. 1993, 94. See also: Paulsen, H.; Bielfeldt, T.; Peters, S.; Bock, K. Liebigs Ann. Chem. 1994, 369.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 1691
    • Chou, S.-S.P.1    Chow, T.J.2    Hsu, C.-H.3    Yang, C.4    Long, S.-H.5    Lin, C.-D.6
  • 12
    • 37049090027 scopus 로고
    • This proposal also accounts for the remarkable observations described in refs 1-3 as well as those in: (a) Marcaurelle, L. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2001, 123, 1587. (b) Elofsson, M.; Salvador, L. A.; Kihlberg, J. Tetrahedron 1997, 53, 369. (c) Chou, S.-S. P.; Chow, T. J.; Hsu, C.-H.; Yang, C.; Long, S.-H.; Lin, C.-D. J. Chem. Soc., Perkin Trans. 1 1997, 1691. (d) McKervey, M. A.; Sullivan, B. O.; Myers, P. L.; Green, R. H. J. Chem. Soc., Chem. Commun. 1993, 94. See also: Paulsen, H.; Bielfeldt, T.; Peters, S.; Bock, K. Liebigs Ann. Chem. 1994, 369.
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 94
    • McKervey, M.A.1    Sullivan, B.O.2    Myers, P.L.3    Green, R.H.4
  • 13
    • 84988080209 scopus 로고
    • This proposal also accounts for the remarkable observations described in refs 1-3 as well as those in: (a) Marcaurelle, L. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2001, 123, 1587. (b) Elofsson, M.; Salvador, L. A.; Kihlberg, J. Tetrahedron 1997, 53, 369. (c) Chou, S.-S. P.; Chow, T. J.; Hsu, C.-H.; Yang, C.; Long, S.-H.; Lin, C.-D. J. Chem. Soc., Perkin Trans. 1 1997, 1691. (d) McKervey, M. A.; Sullivan, B. O.; Myers, P. L.; Green, R. H. J. Chem. Soc., Chem. Commun. 1993, 94. See also: Paulsen, H.; Bielfeldt, T.; Peters, S.; Bock, K. Liebigs Ann. Chem. 1994, 369.
    • (1994) Liebigs Ann. Chem. , pp. 369
    • Paulsen, H.1    Bielfeldt, T.2    Peters, S.3    Bock, K.4
  • 30
    • 0028577168 scopus 로고
    • Park, S.-D.; Oh, J.-H.; Lim, D. Tetrahedron Lett. 2002, 43, 6309. See also: Suh, E. M.; Kishi, Y. J. Am. Chem. Soc. 1994, 116, 11205.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 11205
    • Suh, E.M.1    Kishi, Y.2
  • 31
    • 33845278154 scopus 로고
    • For lead references on azide synthesis, see: (a) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297. (b) Rijkers, D. T. S.; Ricardo van Vugt, H. H.; Jacobs, H. J. F.; Liskamp, R. M. Tetrahedron Lett. 2002, 43, 3657. For thio acid synthesis, see: (c) Goldstein, A. S.; Gelb, M. Tetrahedron Lett. 2000, 41, 2797. (d) Rajagopalan, S.; Radke, G.; Tomich, J. Synth. Commun. 1997, 27, 187. (e) Canne, L.; Walker, S. M.; Kent, S. B. H. Tetrahedron Lett. 1995, 36, 1217. (f) Schwabacher, A. W.; Maynard, T. L. Tetrahedron Lett. 1993, 34, 1269.
    • (1988) Chem. Rev. , vol.88 , pp. 297
    • Scriven, E.F.V.1    Turnbull, K.2
  • 32
    • 0037071180 scopus 로고    scopus 로고
    • For lead references on azide synthesis, see: (a) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297. (b) Rijkers, D. T. S.; Ricardo van Vugt, H. H.; Jacobs, H. J. F.; Liskamp, R. M. Tetrahedron Lett. 2002, 43, 3657. For thio acid synthesis, see: (c) Goldstein, A. S.; Gelb, M. Tetrahedron Lett. 2000, 41, 2797. (d) Rajagopalan, S.; Radke, G.; Tomich, J. Synth. Commun. 1997, 27, 187. (e) Canne, L.; Walker, S. M.; Kent, S. B. H. Tetrahedron Lett. 1995, 36, 1217. (f) Schwabacher, A. W.; Maynard, T. L. Tetrahedron Lett. 1993, 34, 1269.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3657
    • Rijkers, D.T.S.1    Ricardo van Vugt, H.H.2    Jacobs, H.J.F.3    Liskamp, R.M.4
  • 33
    • 0034655782 scopus 로고    scopus 로고
    • For lead references on azide synthesis, see: (a) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297. (b) Rijkers, D. T. S.; Ricardo van Vugt, H. H.; Jacobs, H. J. F.; Liskamp, R. M. Tetrahedron Lett. 2002, 43, 3657. For thio acid synthesis, see: (c) Goldstein, A. S.; Gelb, M. Tetrahedron Lett. 2000, 41, 2797. (d) Rajagopalan, S.; Radke, G.; Tomich, J. Synth. Commun. 1997, 27, 187. (e) Canne, L.; Walker, S. M.; Kent, S. B. H. Tetrahedron Lett. 1995, 36, 1217. (f) Schwabacher, A. W.; Maynard, T. L. Tetrahedron Lett. 1993, 34, 1269.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2797
    • Goldstein, A.S.1    Gelb, M.2
  • 34
    • 0031052803 scopus 로고    scopus 로고
    • For lead references on azide synthesis, see: (a) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297. (b) Rijkers, D. T. S.; Ricardo van Vugt, H. H.; Jacobs, H. J. F.; Liskamp, R. M. Tetrahedron Lett. 2002, 43, 3657. For thio acid synthesis, see: (c) Goldstein, A. S.; Gelb, M. Tetrahedron Lett. 2000, 41, 2797. (d) Rajagopalan, S.; Radke, G.; Tomich, J. Synth. Commun. 1997, 27, 187. (e) Canne, L.; Walker, S. M.; Kent, S. B. H. Tetrahedron Lett. 1995, 36, 1217. (f) Schwabacher, A. W.; Maynard, T. L. Tetrahedron Lett. 1993, 34, 1269.
    • (1997) Synth. Commun. , vol.27 , pp. 187
    • Rajagopalan, S.1    Radke, G.2    Tomich, J.3
  • 35
    • 0028842064 scopus 로고
    • For lead references on azide synthesis, see: (a) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297. (b) Rijkers, D. T. S.; Ricardo van Vugt, H. H.; Jacobs, H. J. F.; Liskamp, R. M. Tetrahedron Lett. 2002, 43, 3657. For thio acid synthesis, see: (c) Goldstein, A. S.; Gelb, M. Tetrahedron Lett. 2000, 41, 2797. (d) Rajagopalan, S.; Radke, G.; Tomich, J. Synth. Commun. 1997, 27, 187. (e) Canne, L.; Walker, S. M.; Kent, S. B. H. Tetrahedron Lett. 1995, 36, 1217. (f) Schwabacher, A. W.; Maynard, T. L. Tetrahedron Lett. 1993, 34, 1269.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 1217
    • Canne, L.1    Walker, S.M.2    Kent, S.B.H.3
  • 36
    • 0027509440 scopus 로고
    • For lead references on azide synthesis, see: (a) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297. (b) Rijkers, D. T. S.; Ricardo van Vugt, H. H.; Jacobs, H. J. F.; Liskamp, R. M. Tetrahedron Lett. 2002, 43, 3657. For thio acid synthesis, see: (c) Goldstein, A. S.; Gelb, M. Tetrahedron Lett. 2000, 41, 2797. (d) Rajagopalan, S.; Radke, G.; Tomich, J. Synth. Commun. 1997, 27, 187. (e) Canne, L.; Walker, S. M.; Kent, S. B. H. Tetrahedron Lett. 1995, 36, 1217. (f) Schwabacher, A. W.; Maynard, T. L. Tetrahedron Lett. 1993, 34, 1269.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1269
    • Schwabacher, A.W.1    Maynard, T.L.2


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