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Volumn 122, Issue 17, 2000, Pages 4005-4010

Notable sulfur atom effects on the regio- and stereoselective formation of oxetanes in Paterno-Buchi photocycloaddition of aromatic aldehydes with silyl O,S-ketene acetals

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETENE DERIVATIVE; OXETANE DERIVATIVE; SULFUR;

EID: 0034600347     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993997i     Document Type: Article
Times cited : (33)

References (70)
  • 4
    • 0001827252 scopus 로고
    • Horspool, W. M., Ed.; Plenum Press: New York
    • (b) Carless, H. A. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: New York, 1984; p 425.
    • (1984) Synthetic Organic Photochemistry , pp. 425
    • Carless, H.A.1
  • 28
    • 0343499454 scopus 로고
    • Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, Chapter 3.1
    • (b) Santamaria, J. In Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part B, Chapter 3.1.
    • (1988) Photoinduced Electron Transfer , Issue.PART B
    • Santamaria, J.1
  • 35
    • 0000981733 scopus 로고
    • The fluorescence of DPA was actually quenched by p-cyanobenzaldehyde 2b, but not by O,S-SKA 1a. For the generation of radical ion pairs by means of such a photosensitization. see; (a) Majima, T. Pac, C.; Sakurai, H. J. Am. Chem. Soc. 1980, 102, 5265. (b) Pac, C. Pure Appl. Chem. 1986, 58, 1249.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5265
    • Majima, T.1    Pac, C.2    Sakurai, H.3
  • 36
    • 0022787684 scopus 로고
    • The fluorescence of DPA was actually quenched by p-cyanobenzaldehyde 2b, but not by O,S-SKA 1a. For the generation of radical ion pairs by means of such a photosensitization. see; (a) Majima, T. Pac, C.; Sakurai, H. J. Am. Chem. Soc. 1980, 102, 5265. (b) Pac, C. Pure Appl. Chem. 1986, 58, 1249.
    • (1986) Pure Appl. Chem. , vol.58 , pp. 1249
    • Pac, C.1
  • 38
    • 0025937149 scopus 로고
    • Stereoselective formation of siloxyoxetanes controlled by product stability, see; (a) Bach, T.; Tetrahedron Lett. 1991, 32, 7037. (b) Bach, T.; Jödicke, K. Chem. Ber. 1993, 126, 2457. (c) Bach, T. Tetrahedron Lett. 1994, 35, 5845. (d) Bach, T. Liebigs Ann. 1995, 855. (e) Bach, T.; Jödicke, K.; Kather, K.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 2437.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 7037
    • Bach, T.1
  • 39
    • 0001313955 scopus 로고
    • Stereoselective formation of siloxyoxetanes controlled by product stability, see; (a) Bach, T.; Tetrahedron Lett. 1991, 32, 7037. (b) Bach, T.; Jödicke, K. Chem. Ber. 1993, 126, 2457. (c) Bach, T. Tetrahedron Lett. 1994, 35, 5845. (d) Bach, T. Liebigs Ann. 1995, 855. (e) Bach, T.; Jödicke, K.; Kather, K.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 2437.
    • (1993) Chem. Ber. , vol.126 , pp. 2457
    • Bach, T.1    Jödicke, K.2
  • 40
    • 0027978622 scopus 로고
    • Stereoselective formation of siloxyoxetanes controlled by product stability, see; (a) Bach, T.; Tetrahedron Lett. 1991, 32, 7037. (b) Bach, T.; Jödicke, K. Chem. Ber. 1993, 126, 2457. (c) Bach, T. Tetrahedron Lett. 1994, 35, 5845. (d) Bach, T. Liebigs Ann. 1995, 855. (e) Bach, T.; Jödicke, K.; Kather, K.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 2437.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 5845
    • Bach, T.1
  • 41
    • 77954271802 scopus 로고
    • Stereoselective formation of siloxyoxetanes controlled by product stability, see; (a) Bach, T.; Tetrahedron Lett. 1991, 32, 7037. (b) Bach, T.; Jödicke, K. Chem. Ber. 1993, 126, 2457. (c) Bach, T. Tetrahedron Lett. 1994, 35, 5845. (d) Bach, T. Liebigs Ann. 1995, 855. (e) Bach, T.; Jödicke, K.; Kather, K.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 2437.
    • (1995) Liebigs Ann. , pp. 855
    • Bach, T.1
  • 42
    • 1842368466 scopus 로고    scopus 로고
    • Stereoselective formation of siloxyoxetanes controlled by product stability, see; (a) Bach, T.; Tetrahedron Lett. 1991, 32, 7037. (b) Bach, T.; Jödicke, K. Chem. Ber. 1993, 126, 2457. (c) Bach, T. Tetrahedron Lett. 1994, 35, 5845. (d) Bach, T. Liebigs Ann. 1995, 855. (e) Bach, T.; Jödicke, K.; Kather, K.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 2437.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2437
    • Bach, T.1    Jödicke, K.2    Kather, K.3    Fröhlich, R.4
  • 43
    • 0004344770 scopus 로고
    • Benjamin/ Cummings. Publishing Co., Inc.: Menlo Park
    • For the concept for regioselectivity of Paternò -Büchi reactions, see; (a) Turro, N. J. Modern Molecular Photochemistry; Benjamin/ Cummings. Publishing Co., Inc.: Menlo Park, 1978; p 432. (b) Sengupta, P.; Chardra, A. K.; Nguyen, M. T. J. Org. Chem. 1997, 62, 6404.
    • (1978) Modern Molecular Photochemistry , pp. 432
    • Turro, N.J.1
  • 44
    • 0000873289 scopus 로고    scopus 로고
    • For the concept for regioselectivity of Paternò -Büchi reactions, see; (a) Turro, N. J. Modern Molecular Photochemistry; Benjamin/ Cummings. Publishing Co., Inc.: Menlo Park, 1978; p 432. (b) Sengupta, P.; Chardra, A. K.; Nguyen, M. T. J. Org. Chem. 1997, 62, 6404.
    • (1997) J. Org. Chem. , vol.62 , pp. 6404
    • Sengupta, P.1    Chardra, A.K.2    Nguyen, M.T.3
  • 46
    • 0343063500 scopus 로고    scopus 로고
    • note
    • PM3 calculations were run on a CAChe system, Sony/Tektonix Co.
  • 49
    • 37049081546 scopus 로고
    • For the regioselective formation of oxetanes from methyl vinylsulfides, see; (a) Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Chem. Commun. 1987, 964. (b) Khan, N.; Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Perkin Trans. 1 1991, 865.
    • (1987) J. Chem. Soc., Chem. Commun. , pp. 964
    • Morris, T.H.1    Smith, E.H.2    Walsh, R.3
  • 50
    • 37049081432 scopus 로고
    • For the regioselective formation of oxetanes from methyl vinylsulfides, see; (a) Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Chem. Commun. 1987, 964. (b) Khan, N.; Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Perkin Trans. 1 1991, 865.
    • (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 865
    • Khan, N.1    Morris, T.H.2    Smith, E.H.3    Walsh, R.4
  • 51
    • 33847803378 scopus 로고
    • For the electrophilic attack, perpendicular approach, of excited carbonyl to electron-rich alkenes, see; (a) Salem, L. J. Am. Chem. Soc. 1974, 96, 3486. (b) Bigot, B.; Devaquet, A.; Turro, N. J. J. Am. Chem. Soc. 1981, 103, 6. Palmer, I. J.; Ragazos, I. N.; Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1994, 116, 2121.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 3486
    • Salem, L.1
  • 52
    • 0006570109 scopus 로고
    • For the electrophilic attack, perpendicular approach, of excited carbonyl to electron-rich alkenes, see; (a) Salem, L. J. Am. Chem. Soc. 1974, 96, 3486. (b) Bigot, B.; Devaquet, A.; Turro, N. J. J. Am. Chem. Soc. 1981, 103, 6. Palmer, I. J.; Ragazos, I. N.; Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1994, 116, 2121.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6
    • Bigot, B.1    Devaquet, A.2    Turro, N.J.3
  • 53
    • 0000625742 scopus 로고
    • For the electrophilic attack, perpendicular approach, of excited carbonyl to electron-rich alkenes, see; (a) Salem, L. J. Am. Chem. Soc. 1974, 96, 3486. (b) Bigot, B.; Devaquet, A.; Turro, N. J. J. Am. Chem. Soc. 1981, 103, 6. Palmer, I. J.; Ragazos, I. N.; Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1994, 116, 2121.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2121
    • Palmer, I.J.1    Ragazos, I.N.2    Bernardi, F.3    Olivucci, M.4    Robb, M.A.5
  • 65
    • 36549100330 scopus 로고
    • For the semiempirical formula for the magnitude of SOC, see; (a) Furlani, T. R.; King, H. F. J. Chem. Phys. 1985, 82, 5577. (b) Carlacci, L.; Doubleday, C., Jr.; Furlani, T. R.; King, H. F.; Mclever, J. W., Jr. J. Am. Chem. Soc. 1987, 109, 5323.
    • (1985) J. Chem. Phys. , vol.82 , pp. 5577
    • Furlani, T.R.1    King, H.F.2


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