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Volumn 118, Issue 20, 1996, Pages 4794-4803

Acid-base properties of arylnitrenium ions

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE;

EID: 0030006665     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954248d     Document Type: Article
Times cited : (131)

References (106)
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    • See also: (i) Abramovitch, R. A.; Cooper, M.; Iyer, S.; Jeyaraman, R.; Rodrigues, J. A. R. J. Org. Chem. 1982, 47, 4819. (j) Abramovitch, R. A.; Jeyaraman, R.; Yannakopoulou, K. J. Chem. Soc., Chem. Commun. 1985, 1017. (k) Abramovitch, R. A.; Hawi, A.; Rodrigues, J. A. R.; Trombretta, T. R. J. Chem. Soc., Chem. Commun. 1986, 283.
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    • See also: (i) Abramovitch, R. A.; Cooper, M.; Iyer, S.; Jeyaraman, R.; Rodrigues, J. A. R. J. Org. Chem. 1982, 47, 4819. (j) Abramovitch, R. A.; Jeyaraman, R.; Yannakopoulou, K. J. Chem. Soc., Chem. Commun. 1985, 1017. (k) Abramovitch, R. A.; Hawi, A.; Rodrigues, J. A. R.; Trombretta, T. R. J. Chem. Soc., Chem. Commun. 1986, 283.
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    • note
    • (a) For details of experiments where the reaction was carried out with varying chloride concentration see ref 24b.
  • 58
    • 15844406246 scopus 로고    scopus 로고
    • note
    • For all three spectra of Figure 1 there was a large negative signal associated with bleaching of the phenyl azide at wavelengths below 270 nm.
  • 61
    • 15844410988 scopus 로고    scopus 로고
    • note
    • 4 was too fast.
  • 65
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    • note
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  • 68
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    • (a) As in the Bamberger rearrangement. For recent references see
    • (a) As in the Bamberger rearrangement. For recent references see:
  • 76
    • 15844384541 scopus 로고    scopus 로고
    • (d) Interestingly, the singlet state that has the lowest energy is an open shell species
    • (d) Interestingly, the singlet state that has the lowest energy is an open shell species.
  • 77
    • 15844381617 scopus 로고    scopus 로고
    • note
    • 12
  • 85
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    • note
    • 24b reacts in a different state of ion pairing, or perhaps in a different vibrational state, when formed from the two precursors.
  • 86
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    • note
    • This is demonstrated in the present experiments by the relatively high yield of the azepinone 22 for the non-nitrenium products.
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    • note
    • 44b
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    • For previous LFP studies involving protonated aromatics see Steenken, S.; McClelland, R. A, J. Am. Chem. Soc. 1990, 112, 9648. Mathivanan, N.; Cozens, F.; McClelland, R. A.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 2198. Lew, C. S. Q.; McClelland, R. A. J. Am. Chem. Soc. 1993, 114, 2198. Zhang, G.; Shi, Y.; Mosi, R.; Ho, T.; Wan. P. Can. J. Chem. 1994, 72, 2388. McClelland, R. A.; Cozens, F.; Steenken, S. Tetrahedron Lett. 1990, 3821.
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    • For previous LFP studies involving protonated aromatics see Steenken, S.; McClelland, R. A, J. Am. Chem. Soc. 1990, 112, 9648. Mathivanan, N.; Cozens, F.; McClelland, R. A.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 2198. Lew, C. S. Q.; McClelland, R. A. J. Am. Chem. Soc. 1993, 114, 2198. Zhang, G.; Shi, Y.; Mosi, R.; Ho, T.; Wan. P. Can. J. Chem. 1994, 72, 2388. McClelland, R. A.; Cozens, F.; Steenken, S. Tetrahedron Lett. 1990, 3821.
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    • For previous LFP studies involving protonated aromatics see Steenken, S.; McClelland, R. A, J. Am. Chem. Soc. 1990, 112, 9648. Mathivanan, N.; Cozens, F.; McClelland, R. A.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 2198. Lew, C. S. Q.; McClelland, R. A. J. Am. Chem. Soc. 1993, 114, 2198. Zhang, G.; Shi, Y.; Mosi, R.; Ho, T.; Wan. P. Can. J. Chem. 1994, 72, 2388. McClelland, R. A.; Cozens, F.; Steenken, S. Tetrahedron Lett. 1990, 3821.
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    • For previous LFP studies involving protonated aromatics see Steenken, S.; McClelland, R. A, J. Am. Chem. Soc. 1990, 112, 9648. Mathivanan, N.; Cozens, F.; McClelland, R. A.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 2198. Lew, C. S. Q.; McClelland, R. A. J. Am. Chem. Soc. 1993, 114, 2198. Zhang, G.; Shi, Y.; Mosi, R.; Ho, T.; Wan. P. Can. J. Chem. 1994, 72, 2388. McClelland, R. A.; Cozens, F.; Steenken, S. Tetrahedron Lett. 1990, 3821.
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    • For previous LFP studies involving protonated aromatics see Steenken, S.; McClelland, R. A, J. Am. Chem. Soc. 1990, 112, 9648. Mathivanan, N.; Cozens, F.; McClelland, R. A.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 2198. Lew, C. S. Q.; McClelland, R. A. J. Am. Chem. Soc. 1993, 114, 2198. Zhang, G.; Shi, Y.; Mosi, R.; Ho, T.; Wan. P. Can. J. Chem. 1994, 72, 2388. McClelland, R. A.; Cozens, F.; Steenken, S. Tetrahedron Lett. 1990, 3821.
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  • 96
    • 15844389559 scopus 로고    scopus 로고
    • note
    • -OH cannot separate.
  • 97
    • 15844391708 scopus 로고    scopus 로고
    • note
    • The experiments measuring this quantity reported in Table 2 were carried out in such a way that the ΔOD values represent relative quantum yields for formation of the transient.
  • 98
    • 15844392438 scopus 로고    scopus 로고
    • note
    • 48b
  • 99
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    • Personal communication
    • (b) Novak, M. Personal communication.
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  • 101
    • 15844420930 scopus 로고    scopus 로고
    • note
    • w employed previously.
  • 102
    • 15844407563 scopus 로고    scopus 로고
    • note
    • obs(N-acetyl) refers to the same acid.
  • 103
    • 15844430670 scopus 로고    scopus 로고
    • 52h
    • 52h


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.