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Volumn 118, Issue 1, 1996, Pages 13-19

Absolute kinetics of aminium radical reactions with olefins in acetonitrile solution

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EID: 0002102255     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja950133y     Document Type: Article
Times cited : (64)

References (51)
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    • (1994) Tetrahedron , vol.50 , pp. 1275-1294
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    • (1991) Aust. J. Chem. , vol.44 , pp. 1809-1812
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    • Bowman, W. R.; Clark, D N.; Marmon, R. J. Tetrahedron Lett. 1991, 32, 6441-6444. Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron 1994, 50, 1275-1294 and 1295-1310. Beckwith, A. L. J.; Maxwell, B. J.; Tsanaktsidis, J. Aust. J. Chem. 1991, 44, 1809-1812. Murphy, J. A.; Dickinson, J. M. Tetrahedron 1992, 48, 1317-1326. Schwan, A. L.; Refvik, M. D. Tetrahedron Lett. 1993, 32, 4901-4904. Dekimpe, N.; Desmaele, D ; Bogaert. P. Synlett 1994, 287-288.
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  • 15
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    • Fischer, H., Ed.; Springer-Verlag: Berlin
    • What little kinetic data on aminium radical reactions is available is summarized in the following: Ingold, K. U. In Radical Reaction Rates in Liquids; Fischer, H., Ed.; Springer-Verlag: Berlin, 1983; Vol. 13, subvolume c, and 1994, Vol. 18, subvolume c.
    • (1983) Radical Reaction Rates in Liquids , vol.13-18 SUBVOLUME C
    • Ingold, K.U.1
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    • note
    • Other less thoroughly examined N-nitrosamines studied included di-n-propylnitrosamine. 1-nitrosopytrolidine, and n-propyl-n-butylnitrosamine which upon 266 nm LFP of 0.05 M maleic acid/acetonitrile solutions gave transient absorptions very similar to those shown in Figure 1a.b with aminium radicals lifetimes of 2.3. 2.6, and 1.8 μs, respectively.
  • 36
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    • note
    • It has to be noted, however, that the spectra of the aminyl radicals 3b and 4b observed upon photolysis of the nitrosamines 3a and 4a (numbering system given in Table 1 and illustrated in Scheme 1) in the absence of acid (vide infra) were also unaffected by the presence of oxygen.
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    • note
    • -1 for TFA and MA, respectively. More precise measurements of these and other related equilibrium constants will be presented later.
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    • note
    • 33
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    • Maxwell, J. B.; Schiesser, C. H.; Smart, B. A.; Tsanaktsidis, J. J. Chem. Soc., Perkin Trans. 2 1994, 2385-2387; J. Chem. Soc., Perkin Trans. 2 1995, 1245.
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 1245


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