Mechanistic Evaluation of the Transfer of Br+ from Bis(sym-collidine)bromonium Triflate to Acceptor Alkenes

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5977-5982

  Neverov, Alexei A ^a   Brown, R S ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001765423     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980627o     Document Type: Article

References (28)

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15. Perrin, D. D.; Armagero, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2nd ed.; Pergamon Press: Oxford, 1980; p 204.
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22. +-coll complex. Although the final product is the bromomethyltetrahydrofuran, we do not know whether it is produced from the corresponding bromo triflate, or by direct intramolecular capture of the bromonium ion. On the basis of our previous results, the latter seems more likely.
23. - are fit to eq 2, we noticed that the fit was not satisfactory. Treatment according to eq 3 produced satisfactory fits.
24. Zhang, C. Y.; Slebocka-Tilk, H.; Nagorski, R. W.; Alvarado, L.; Brown, R. S. J. Org. Chem. 1993, 58, 2122.
25. Zefirov, N. S.; Koz'min, A. S.; Sorokin, V. D.; Zdankin, V. V. J. Org. Chem. USSR (Engl. Transl.) 1982, 18, 1546.
26. For a detailed discussion of this process in brommation, see: Slebocka-Tilk, H.; Zheng, C. Y.; Brown, R. S. J. Am. Chem. Soc. 1993, 115, 1347. Koerner, T.; Brown, R. S.; Gainsforth, J. L.; Klobukowski, M. J. Am. Chem. Soc. 1998, 120, 5628.
27. For a detailed discussion of this process in brommation, see: Slebocka-Tilk, H.; Zheng, C. Y.; Brown, R. S. J. Am. Chem. Soc. 1993, 115, 1347. Koerner, T.; Brown, R. S.; Gainsforth, J. L.; Klobukowski, M. J. Am. Chem. Soc. 1998, 120, 5628.
28. -4 M.