메뉴 건너뛰기




Volumn 101, Issue 51, 1997, Pages 10082-10089

Structural, spectroscopic, and theoretical study of 1-acetylvinyl p-nitrobenzoate, a highly reactive and selective captodative olefin in cycloaddition reactions

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CALCULATIONS; CONFORMATIONS; CORRELATION METHODS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; X RAY CRYSTALLOGRAPHY;

EID: 0031355495     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp972707m     Document Type: Article
Times cited : (30)

References (80)
  • 9
    • 0003667457 scopus 로고
    • American Chemical Society: Washington, DC
    • Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. Natural Products Synthesis through Pericyclic Reactions; American Chemical Society: Washington, DC, 1983. Beraldi, P. G.; Barco, A.; Benetti, S.; Pollini, G. P.; Simoni, D. Synthesis 1987, 857. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. Oh, T.; Reilly, M. Org. Prep. Proc. Int. 1994, 26, 129.
    • (1983) Natural Products Synthesis Through Pericyclic Reactions
    • Desimoni, G.1    Tacconi, G.2    Barco, A.3    Pollini, G.P.4
  • 10
    • 0023618387 scopus 로고
    • Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. Natural Products Synthesis through Pericyclic Reactions; American Chemical Society: Washington, DC, 1983. Beraldi, P. G.; Barco, A.; Benetti, S.; Pollini, G. P.; Simoni, D. Synthesis 1987, 857. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. Oh, T.; Reilly, M. Org. Prep. Proc. Int. 1994, 26, 129.
    • (1987) Synthesis , pp. 857
    • Beraldi, P.G.1    Barco, A.2    Benetti, S.3    Pollini, G.P.4    Simoni, D.5
  • 11
    • 0003523008 scopus 로고
    • Pergamon Press: Oxford
    • Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. Natural Products Synthesis through Pericyclic Reactions; American Chemical Society: Washington, DC, 1983. Beraldi, P. G.; Barco, A.; Benetti, S.; Pollini, G. P.; Simoni, D. Synthesis 1987, 857. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. Oh, T.; Reilly, M. Org. Prep. Proc. Int. 1994, 26, 129.
    • (1990) Cycloaddition Reactions in Organic Synthesis
    • Carruthers, W.1
  • 12
    • 0342360660 scopus 로고
    • Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. Natural Products Synthesis through Pericyclic Reactions; American Chemical Society: Washington, DC, 1983. Beraldi, P. G.; Barco, A.; Benetti, S.; Pollini, G. P.; Simoni, D. Synthesis 1987, 857. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. Oh, T.; Reilly, M. Org. Prep. Proc. Int. 1994, 26, 129.
    • (1994) Org. Prep. Proc. Int. , vol.26 , pp. 129
    • Oh, T.1    Reilly, M.2
  • 28
    • 0021526965 scopus 로고
    • Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876. Oppolzer, W. Tetrahedron 1987, 43, 1969. Oppolzer, W.; Chapuis, C. Tetrahedron Lett. 1983, 24, 4665. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 876
    • Oppolzer, W.1
  • 29
    • 0038736789 scopus 로고
    • Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876. Oppolzer, W. Tetrahedron 1987, 43, 1969. Oppolzer, W.; Chapuis, C. Tetrahedron Lett. 1983, 24, 4665. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
    • (1987) Tetrahedron , vol.43 , pp. 1969
    • Oppolzer, W.1
  • 30
    • 1542508435 scopus 로고
    • Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876. Oppolzer, W. Tetrahedron 1987, 43, 1969. Oppolzer, W.; Chapuis, C. Tetrahedron Lett. 1983, 24, 4665. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4665
    • Oppolzer, W.1    Chapuis, C.2
  • 31
    • 0000998377 scopus 로고
    • Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876. Oppolzer, W. Tetrahedron 1987, 43, 1969. Oppolzer, W.; Chapuis, C. Tetrahedron Lett. 1983, 24, 4665. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 3095
    • Poll, T.1    Sobczak, A.2    Hartmann, H.3    Helmchen, G.4
  • 32
    • 0000909681 scopus 로고
    • Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876. Oppolzer, W. Tetrahedron 1987, 43, 1969. Oppolzer, W.; Chapuis, C. Tetrahedron Lett. 1983, 24, 4665. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 4261
    • Evans, D.A.1    Chapman, K.T.2    Bisaha, J.3
  • 33
    • 33845280186 scopus 로고
    • Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876. Oppolzer, W. Tetrahedron 1987, 43, 1969. Oppolzer, W.; Chapuis, C. Tetrahedron Lett. 1983, 24, 4665. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1238
    • Evans, D.A.1    Chapman, K.T.2    Bisaha, J.3
  • 38
    • 84981955204 scopus 로고
    • Sustmann, R.; Schubert, R. Angew. Chem., Int. Ed. Engl. 1972, 11, 840. Sustmann, R.; Trill, H. Angew. Chem., Int. Ed. Engl. 1972, 11, 838. Blain, M.; Odiot, S.; Martin, G. J.; Gouesnard, J. P.; Chalvet, O. Tetrahedron 1980, 36, 2775.
    • (1972) Angew. Chem., Int. Ed. Engl. , vol.11 , pp. 840
    • Sustmann, R.1    Schubert, R.2
  • 39
    • 84981944885 scopus 로고
    • Sustmann, R.; Schubert, R. Angew. Chem., Int. Ed. Engl. 1972, 11, 840. Sustmann, R.; Trill, H. Angew. Chem., Int. Ed. Engl. 1972, 11, 838. Blain, M.; Odiot, S.; Martin, G. J.; Gouesnard, J. P.; Chalvet, O. Tetrahedron 1980, 36, 2775.
    • (1972) Angew. Chem., Int. Ed. Engl. , vol.11 , pp. 838
    • Sustmann, R.1    Trill, H.2
  • 40
    • 4043169208 scopus 로고
    • Sustmann, R.; Schubert, R. Angew. Chem., Int. Ed. Engl. 1972, 11, 840. Sustmann, R.; Trill, H. Angew. Chem., Int. Ed. Engl. 1972, 11, 838. Blain, M.; Odiot, S.; Martin, G. J.; Gouesnard, J. P.; Chalvet, O. Tetrahedron 1980, 36, 2775.
    • (1980) Tetrahedron , vol.36 , pp. 2775
    • Blain, M.1    Odiot, S.2    Martin, G.J.3    Gouesnard, J.P.4    Chalvet, O.5
  • 43
    • 14344276434 scopus 로고
    • Sanche, J.; Schulz, G. J. Phys. Rev. 1972, A5, 1672. Schulz, G. J. Rev. Mod. Phys. 1973, 45, 378. Schulz, G. J. Rev. Mod. Phys. 1973, 45, 423.
    • (1972) Phys. Rev. , vol.A5 , pp. 1672
    • Sanche, J.1    Schulz, G.J.2
  • 44
    • 35949028579 scopus 로고
    • Sanche, J.; Schulz, G. J. Phys. Rev. 1972, A5, 1672. Schulz, G. J. Rev. Mod. Phys. 1973, 45, 378. Schulz, G. J. Rev. Mod. Phys. 1973, 45, 423.
    • (1973) Rev. Mod. Phys. , vol.45 , pp. 378
    • Schulz, G.J.1
  • 45
    • 22244433042 scopus 로고
    • Sanche, J.; Schulz, G. J. Phys. Rev. 1972, A5, 1672. Schulz, G. J. Rev. Mod. Phys. 1973, 45, 378. Schulz, G. J. Rev. Mod. Phys. 1973, 45, 423.
    • (1973) Rev. Mod. Phys. , vol.45 , pp. 423
    • Schulz, G.J.1
  • 53
    • 5644256244 scopus 로고    scopus 로고
    • unpublished results
    • Modelli, A., unpublished results.
    • Modelli, A.1
  • 56
    • 0002313438 scopus 로고
    • Fukui, K. Acc. Chem. Res 1971, 4, 57. Alston, P. V.; Ottenbrite, R. M.; Shillady, D. D. J. Org. Chem. 1973, 38, 4075. Eisenstein, O.; Lefour, J. M.; Anh, N. T.; Hudson, R. F. Tetrahedron 1977, 33, 523. Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4092.
    • (1971) Acc. Chem. Res , vol.4 , pp. 57
    • Fukui, K.1
  • 57
    • 0006379679 scopus 로고
    • Fukui, K. Acc. Chem. Res 1971, 4, 57. Alston, P. V.; Ottenbrite, R. M.; Shillady, D. D. J. Org. Chem. 1973, 38, 4075. Eisenstein, O.; Lefour, J. M.; Anh, N. T.; Hudson, R. F. Tetrahedron 1977, 33, 523. Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4092.
    • (1973) J. Org. Chem. , vol.38 , pp. 4075
    • Alston, P.V.1    Ottenbrite, R.M.2    Shillady, D.D.3
  • 58
    • 0000907742 scopus 로고
    • Fukui, K. Acc. Chem. Res 1971, 4, 57. Alston, P. V.; Ottenbrite, R. M.; Shillady, D. D. J. Org. Chem. 1973, 38, 4075. Eisenstein, O.; Lefour, J. M.; Anh, N. T.; Hudson, R. F. Tetrahedron 1977, 33, 523. Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4092.
    • (1977) Tetrahedron , vol.33 , pp. 523
    • Eisenstein, O.1    Lefour, J.M.2    Anh, N.T.3    Hudson, R.F.4
  • 59
    • 0001490550 scopus 로고
    • Fukui, K. Acc. Chem. Res 1971, 4, 57. Alston, P. V.; Ottenbrite, R. M.; Shillady, D. D. J. Org. Chem. 1973, 38, 4075. Eisenstein, O.; Lefour, J. M.; Anh, N. T.; Hudson, R. F. Tetrahedron 1977, 33, 523. Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4092.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 4092
    • Houk, K.N.1
  • 60
    • 0030837872 scopus 로고    scopus 로고
    • and references therein
    • Damoun, S.; Van de Woude, G.; Méndez, F.; Geerlings, P. J. Phys. Chem. A 1997, 101, 886 and references therein. Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381. Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663.
    • (1997) J. Phys. Chem. A , vol.101 , pp. 886
    • Damoun, S.1    Van De Woude, G.2    Méndez, F.3    Geerlings, P.4
  • 61
    • 33845373869 scopus 로고
    • Damoun, S.; Van de Woude, G.; Méndez, F.; Geerlings, P. J. Phys. Chem. A 1997, 101, 886 and references therein. Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381. Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7381
    • Kahn, S.D.1    Pau, C.F.2    Overman, L.E.3    Hehre, W.J.4
  • 62
    • 0344803578 scopus 로고
    • Damoun, S.; Van de Woude, G.; Méndez, F.; Geerlings, P. J. Phys. Chem. A 1997, 101, 886 and references therein. Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381. Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 663
    • Kahn, S.D.1    Hehre, W.J.2
  • 64
    • 8444231677 scopus 로고
    • Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1975. Sustmann, R. Tetrahedron Lett. 1971, 2721.
    • (1971) Tetrahedron Lett. , pp. 2721
    • Sustmann, R.1
  • 66
    • 0000560633 scopus 로고
    • Fox, M. A.; Cardona, R.; Kiwiet, N. J. J. Org. Chem. 1987, 52, 1469. Bachler, V.; Mark, F. Theor. Chim. Acta 1976, 43, 121 and references therein. Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257.
    • (1987) J. Org. Chem. , vol.52 , pp. 1469
    • Fox, M.A.1    Cardona, R.2    Kiwiet, N.J.3
  • 67
    • 1542797310 scopus 로고
    • and references therein
    • Fox, M. A.; Cardona, R.; Kiwiet, N. J. J. Org. Chem. 1987, 52, 1469. Bachler, V.; Mark, F. Theor. Chim. Acta 1976, 43, 121 and references therein. Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257.
    • (1976) Theor. Chim. Acta , vol.43 , pp. 121
    • Bachler, V.1    Mark, F.2
  • 68
    • 33845279009 scopus 로고
    • Fox, M. A.; Cardona, R.; Kiwiet, N. J. J. Org. Chem. 1987, 52, 1469. Bachler, V.; Mark, F. Theor. Chim. Acta 1976, 43, 121 and references therein. Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 3257
    • Tripathy, R.1    Franck, R.W.2    Onan, K.D.3
  • 70
    • 0011701784 scopus 로고
    • 3a remains controversial: Pasto, D. J. J. Org. Chem. 1992, 57, 1139.
    • (1992) J. Org. Chem. , vol.57 , pp. 1139
    • Pasto, D.J.1
  • 72
    • 0001187298 scopus 로고
    • Huisgen, R.; Mioston, G.; Langhals, E. J. Am. Chem. Soc. 1986, 108, 6401. Huisgen, R.; Mloston, G.; Langhals, E. J. Org. Chem. 1986, 51, 4085. Mloston, G.; Langhals, E.; Huisgen, R. Tetrahedron Lett. 1989, 30, 5373. Firestone, R. A. J. Org. Chem. 1968, 33, 2285. Firestone, R. A. J. Org. Chem. 1972, 37, 2181. Firestone, R. A. Tetrahedron 1977,33, 3009.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6401
    • Huisgen, R.1    Mioston, G.2    Langhals, E.3
  • 73
    • 0000369902 scopus 로고
    • Huisgen, R.; Mioston, G.; Langhals, E. J. Am. Chem. Soc. 1986, 108, 6401. Huisgen, R.; Mloston, G.; Langhals, E. J. Org. Chem. 1986, 51, 4085. Mloston, G.; Langhals, E.; Huisgen, R. Tetrahedron Lett. 1989, 30, 5373. Firestone, R. A. J. Org. Chem. 1968, 33, 2285. Firestone, R. A. J. Org. Chem. 1972, 37, 2181. Firestone, R. A. Tetrahedron 1977,33, 3009.
    • (1986) J. Org. Chem. , vol.51 , pp. 4085
    • Huisgen, R.1    Mloston, G.2    Langhals, E.3
  • 74
    • 0001720248 scopus 로고
    • Huisgen, R.; Mioston, G.; Langhals, E. J. Am. Chem. Soc. 1986, 108, 6401. Huisgen, R.; Mloston, G.; Langhals, E. J. Org. Chem. 1986, 51, 4085. Mloston, G.; Langhals, E.; Huisgen, R. Tetrahedron Lett. 1989, 30, 5373. Firestone, R. A. J. Org. Chem. 1968, 33, 2285. Firestone, R. A. J. Org. Chem. 1972, 37, 2181. Firestone, R. A. Tetrahedron 1977,33, 3009.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 5373
    • Mloston, G.1    Langhals, E.2    Huisgen, R.3
  • 75
    • 33947317869 scopus 로고
    • Huisgen, R.; Mioston, G.; Langhals, E. J. Am. Chem. Soc. 1986, 108, 6401. Huisgen, R.; Mloston, G.; Langhals, E. J. Org. Chem. 1986, 51, 4085. Mloston, G.; Langhals, E.; Huisgen, R. Tetrahedron Lett. 1989, 30, 5373. Firestone, R. A. J. Org. Chem. 1968, 33, 2285. Firestone, R. A. J. Org. Chem. 1972, 37, 2181. Firestone, R. A. Tetrahedron 1977,33, 3009.
    • (1968) J. Org. Chem. , vol.33 , pp. 2285
    • Firestone, R.A.1
  • 76
    • 0001057190 scopus 로고
    • Huisgen, R.; Mioston, G.; Langhals, E. J. Am. Chem. Soc. 1986, 108, 6401. Huisgen, R.; Mloston, G.; Langhals, E. J. Org. Chem. 1986, 51, 4085. Mloston, G.; Langhals, E.; Huisgen, R. Tetrahedron Lett. 1989, 30, 5373. Firestone, R. A. J. Org. Chem. 1968, 33, 2285. Firestone, R. A. J. Org. Chem. 1972, 37, 2181. Firestone, R. A. Tetrahedron 1977,33, 3009.
    • (1972) J. Org. Chem. , vol.37 , pp. 2181
    • Firestone, R.A.1
  • 77
    • 0347015215 scopus 로고
    • Huisgen, R.; Mioston, G.; Langhals, E. J. Am. Chem. Soc. 1986, 108, 6401. Huisgen, R.; Mloston, G.; Langhals, E. J. Org. Chem. 1986, 51, 4085. Mloston, G.; Langhals, E.; Huisgen, R. Tetrahedron Lett. 1989, 30, 5373. Firestone, R. A. J. Org. Chem. 1968, 33, 2285. Firestone, R. A. J. Org. Chem. 1972, 37, 2181. Firestone, R. A. Tetrahedron 1977,33, 3009.
    • (1977) Tetrahedron , vol.33 , pp. 3009
    • Firestone, R.A.1
  • 78
    • 0004150157 scopus 로고
    • Siemens Energy & Automation, Germany
    • SHELXTL, v. 5.03, Siemens Energy & Automation, Germany, 1995.
    • (1995) SHELXTL, v. 5.03
  • 79
    • 1542797316 scopus 로고    scopus 로고
    • WaveFunction Inc., 18401 VonKarman, Suite 370, Irvine, CA 92715
    • MacSpartan, v. 1.0, WaveFunction Inc., 18401 VonKarman, Suite 370, Irvine, CA 92715.
    • MacSpartan, v. 1.0


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.