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Volumn 62, Issue 10, 1997, Pages 3055-3061

Photochemical Reactions of Mesityl Azide with Tetracyanoethylene: Competitive Trapping of Singlet Nitrene and Didehydroazepine

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EID: 0000899656     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9622901     Document Type: Article
Times cited : (50)

References (34)
  • 1
    • 0001338830 scopus 로고
    • The photochemistry of aryl azides has reviewed; see, for example: (a) Iddon, B.; Meth-Cohn, O.; Scriven, E. F. V.; Suschitzky, H.; Gallagher, P. T. Angew. Chem., Int. Ed. Engl. 1979, 18, 900. (b) Scriven, E. F. V. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1982. Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic Press: New York, 1984. Wentrup, C. Reactive Molecules; Wiley: New York, 1984; Chapter 4.
    • (1979) Angew. Chem., Int. Ed. Engl. , vol.18 , pp. 900
    • Iddon, B.1    Meth-Cohn, O.2    Scriven, E.F.V.3    Suschitzky, H.4    Gallagher, P.T.5
  • 2
    • 0001338830 scopus 로고
    • Abramovitch, R. A., Ed.; Plenum Press: New York
    • The photochemistry of aryl azides has reviewed; see, for example: (a) Iddon, B.; Meth-Cohn, O.; Scriven, E. F. V.; Suschitzky, H.; Gallagher, P. T. Angew. Chem., Int. Ed. Engl. 1979, 18, 900. (b) Scriven, E. F. V. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1982. Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic Press: New York, 1984. Wentrup, C. Reactive Molecules; Wiley: New York, 1984; Chapter 4.
    • (1982) Reactive Intermediates
    • Scriven, E.F.V.1
  • 3
    • 0001338830 scopus 로고
    • Academic Press: New York
    • The photochemistry of aryl azides has reviewed; see, for example: (a) Iddon, B.; Meth-Cohn, O.; Scriven, E. F. V.; Suschitzky, H.; Gallagher, P. T. Angew. Chem., Int. Ed. Engl. 1979, 18, 900. (b) Scriven, E. F. V. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1982. Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic Press: New York, 1984. Wentrup, C. Reactive Molecules; Wiley: New York, 1984; Chapter 4.
    • (1984) Azides and Nitrenes
    • Scriven, E.F.V.1
  • 4
    • 0001338830 scopus 로고
    • Wiley: New York, Chapter 4
    • The photochemistry of aryl azides has reviewed; see, for example: (a) Iddon, B.; Meth-Cohn, O.; Scriven, E. F. V.; Suschitzky, H.; Gallagher, P. T. Angew. Chem., Int. Ed. Engl. 1979, 18, 900. (b) Scriven, E. F. V. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1982. Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic Press: New York, 1984. Wentrup, C. Reactive Molecules; Wiley: New York, 1984; Chapter 4.
    • (1984) Reactive Molecules
    • Wentrup, C.1
  • 22
    • 0000793834 scopus 로고
    • The electronic influence of the azido group on an aromatic ring should be also considered. At the present time, however, little is known about the electronic character of the azido group because of its high reactivity. Smith and his co-workers reported that the azido group strengthened the acidity of benzoic acid, while electrophilic aromatic substitution was markedly activated by the azido substitution: Smith, P. A. S.; Hall, J. H.; Kan, R. O. J. Am. Chem. Soc. 1962, 84, 485.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 485
    • Smith, P.A.S.1    Hall, J.H.2    Kan, R.O.3
  • 25
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    • 2: (a) Spada, L. T.; Foote, C. S. J. Am. Chem. Soc. 1980, 102, 391. (b) Akaba, R.; Kamata, M.; Sakuragi, H.; Tokumaru, K. Tetrahedron Lett. 1992, 33, 8105. Murata, S.; Nakatsuji, R.; Tomioka, H. J. Chem. Soc., Perkin Trans. 2 1995, 793.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 391
    • Spada, L.T.1    Foote, C.S.2
  • 26
    • 0027048605 scopus 로고
    • 2: (a) Spada, L. T.; Foote, C. S. J. Am. Chem. Soc. 1980, 102, 391. (b) Akaba, R.; Kamata, M.; Sakuragi, H.; Tokumaru, K. Tetrahedron Lett. 1992, 33, 8105. Murata, S.; Nakatsuji, R.; Tomioka, H. J. Chem. Soc., Perkin Trans. 2 1995, 793.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 8105
    • Akaba, R.1    Kamata, M.2    Sakuragi, H.3    Tokumaru, K.4
  • 27
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    • 2: (a) Spada, L. T.; Foote, C. S. J. Am. Chem. Soc. 1980, 102, 391. (b) Akaba, R.; Kamata, M.; Sakuragi, H.; Tokumaru, K. Tetrahedron Lett. 1992, 33, 8105. Murata, S.; Nakatsuji, R.; Tomioka, H. J. Chem. Soc., Perkin Trans. 2 1995, 793.
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 793
    • Murata, S.1    Nakatsuji, R.2    Tomioka, H.3
  • 29
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    • note
    • -1, which was based on the assumption that the rate constant for the protonation of 2S was equal to that of alkylamines: ref 7b.
  • 30
    • 0003428791 scopus 로고
    • Wiley: New York
    • For reviews on carbene chemistry, see, for example: (a) Carbenes; Moss, R. A., Jones, M., Jr., Eds.; Wiley: New York, 1973, 1975; Vols. 1 and 2. (b) Kirmse, W. Carbene Chemistry; Academic Press: New York, 1971. See also ref 1d.
    • (1973) Carbenes , vol.1-2
    • Moss, R.A.1    Jones Jr., M.2
  • 31
    • 0004050551 scopus 로고
    • Academic Press: New York, See also ref 1d
    • For reviews on carbene chemistry, see, for example: (a) Carbenes; Moss, R. A., Jones, M., Jr., Eds.; Wiley: New York, 1973, 1975; Vols. 1 and 2. (b) Kirmse, W. Carbene Chemistry; Academic Press: New York, 1971. See also ref 1d.
    • (1971) Carbene Chemistry
    • Kirmse, W.1
  • 34
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    • Wiley: New York; Collect.
    • Carboni, R. A. Organic Synsesis; Wiley: New York, 1963; Collect. Vol. IV, p 877.
    • (1963) Organic Synsesis , vol.4 , pp. 877
    • Carboni, R.A.1


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