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Volumn , Issue 12, 1998, Pages 2735-2739

Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3 + 2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions

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EID: 0002145471     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805308a     Document Type: Article
Times cited : (20)

References (48)
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    • Part of the PhD Thesis of Carsten Gaebert, Westfälische Wilhelm-Universität Münster, 1997.
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    • (a) R. Huisgen, Angew. Chem., 1963, 75, 604; Angew. Chem., Int. Ed. Engl., 1963, 2, 633;
    • (1963) Angew. Chem., Int. Ed. Engl. , vol.2 , pp. 633
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    • a-value of pure water
    • a-value of pure water.
  • 28
    • 0000605895 scopus 로고
    • Iminium ions of a completely different structure have recently been produced by solvolysis of anilinothioethers (S. Eldin and W. P. Jencks, J. Am. Chem. Soc., 1995, 117, 4851).
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4851
    • Eldin, S.1    Jencks, W.P.2
  • 29
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    • max of this ion is lower than that (280 nm) from 1 may be due to the higher electron density in the latter case
    • max of this ion is lower than that (280 nm) from 1 may be due to the higher electron density in the latter case.
  • 30
    • 0345957392 scopus 로고    scopus 로고
    • This higher value as compared to 1 may indicate a higher degree of linearity of the transition state
    • This higher value as compared to 1 may indicate a higher degree of linearity of the transition state.
  • 31
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    • It is likely that the charge distribution in the ylides is different for 1-2 as compared to 3-5. With 1 and 2, the negative charge is localized equally on the equivalent benzylic carbons, whereas in 3-5 it is probably located on the single benzylic carbon, as indicated in Scheme 1
    • It is likely that the charge distribution in the ylides is different for 1-2 as compared to 3-5. With 1 and 2, the negative charge is localized equally on the equivalent benzylic carbons, whereas in 3-5 it is probably located on the single benzylic carbon, as indicated in Scheme 1.
  • 34
    • 0346588697 scopus 로고
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    • (a) Evelyn Albrecht, PhD Thesis, Westfälische Wilhelm-Universität Münster, 1995;
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    • (g) A. Rainis, R. Tung and M. Szwarc, J. Am. Chem. Soc., 1973, 95, 659. For a detailed discussion of similar phenomena see W. Kirmse, M. Guth and S. Steenken, J. Am. Chem. Soc., 1996, 118, 10838.
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    • Rainis, A.1    Tung, R.2    Szwarc, M.3
  • 41
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    • (g) A. Rainis, R. Tung and M. Szwarc, J. Am. Chem. Soc., 1973, 95, 659. For a detailed discussion of similar phenomena see W. Kirmse, M. Guth and S. Steenken, J. Am. Chem. Soc., 1996, 118, 10838.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10838
    • Kirmse, W.1    Guth, M.2    Steenken, S.3
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    • Starting with commercially available 2-phenyloxirane the corresponding β-amino alcohol was prepared according to the procedure of N. B. Chapman and D. J. Triggle, J. Chem. Soc., 1963, 1385; 1-butyl-2-phenylaziridine was prepared as described by I. Okada, K. Ichimura and R. Sudo, Bull. Chem. Soc. Jpn., 1970, 43, 1185.
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    • Chapman, N.B.1    Triggle, D.J.2
  • 46
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    • Starting with commercially available 2-phenyloxirane the corresponding β-amino alcohol was prepared according to the procedure of N. B. Chapman and D. J. Triggle, J. Chem. Soc., 1963, 1385; 1-butyl-2-phenylaziridine was prepared as described by I. Okada, K. Ichimura and R. Sudo, Bull. Chem. Soc. Jpn., 1970, 43, 1185.
    • (1970) Bull. Chem. Soc. Jpn. , vol.43 , pp. 1185
    • Okada, I.1    Ichimura, K.2    Sudo, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.