1-Alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts: A novel family of electrophilic fluorinating agents

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 8, 1992, Pages 595-596

  Banks, R Eric ^a   Mohialdin Khaffaf, Suad N ^a   Lal, G Sankar ^b   Sharif, Iqbal ^a   Syvret, Robert G ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b AIR PRODUCTS AND CHEMICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049071468     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39920000595     Document Type: Conference Paper

References (21)

1. Oral presentation at the 13th International Symposium on Fluorine Chemistry (see R. E. Banks, G. S. Lal, abstracts D20 and D21, J. Fluorine Chem., 1991, 54, 207). The new +N-F compounds described here are members of Air Products and Chemicals, Selectfluor family of fluorinating agents; information regarding availability and applications is available from Mr T. A. Shenoy, Air Products and Chemicals Inc., 7201 Hamilton Boulevard, Allentown, PA 18195–1501, USA.
2. J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, John Wiley, New York, 1991.
3. M. R. Kilbourn, Fluorine-18 Labeling of Radiopharmaceuticals, National Academy Press, Washington DC, 1990.
4. For a recent review of electrophilic fluorination, see G. G. Furin in New Fluorinating Agents in Organic Syntheses, ed. L. German and S. Zemskov, Springer-Verlag, Berlin, 1989, pp. 34–68; note that extensive lists of primary literature appear in refs. 9 and 11a.
5. C. M. Sharts and W. A. Sheppard, Org. React., 1974, 21, 225.
6. F. M. Mukametshin, ref. 4, pp. 59–116.
7. V. V. Bardin and Yu. L. Yagupolskii, ref. 4. pp. 1–34.
8. S. T. Purrington, B. S. Kagen and T. B. Patrick, Chem. Rev., 1986, 86, 997.
9. V. Murtagh, Perform. Chem., 1991, 6435.
10. R. E. Banks, V. Murtagh and E. Tsiliopoulos, J. Fluorine Chem., 1991, 52, 389.
11. G. Resnati and D. D. DesMarteau, J. Org. Chem., 1991, 56, 4925.
12. M. Van Der Puy, D. Nalewajek, G. A. Shia and W. J. Wagner, US Pat. 4,935, 519/1990;.
13. A. J. Poss, M. Van Der Puy, D. Nalewajek, G. A. Shia, W. J. Wagner and R. L. Frenette, J. Org. Chem., 1991, 56, 5962.
14. Note, however, that our analysis (including an X-ray study) of a commercial sample of so-called N-fluoropyridinium pyridine heptafluorodiborate indicates that the material is N-fluoropyridinium pyridinium tetrafluoroborate trifluorohydroxyborate (R. E. Banks, M. K. Besheesh and R. Pritchard, in preparation).
15. R. E. Banks, R. A. Du Boisson, W. D. Morton and E. Tsiliopoulos, J. Chem. Soc., Perkin Trans. I, 1988, 2805.
16. R. E. Banks and I. Sharif, J. Fluorine Chem., 1988, 41, 297.
17. R. E. Banks and I. Sharif, J. Fluorine Chem., 1992, 55, 207.
18. R. E. Banks and E. Tsiliopoulos, unpublished resuls;.
19. E. Tsiliopoulos, PhD Thesis, University of Manchester, 1986.
20. R. E. Banks, R. G. Pritchard and I. Sharif, in preparation.
21. –) decomposes exothermally on heating, beginning at 190 °C.