Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl

Journal of Organic Chemistry

Volumn 63, Issue 1, 1998, Pages 36-43

  Krespan, Carl G ^a   Dixon, David A ^b  

^a DUPONT COMPANY   (United States)

^b PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011830979     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970805y     Document Type: Article

References (23)

1. Krespan, C. G. J. Fluorine Chem. 1988, 40, 129.
2. Krespan, C. G. J. Fluorine Chem. 1994, 66, 311.
3. F; see, for example, the following: McBride, D. W.; Stafford, S. L.; Stone, F. G. A. J. Chem. Soc. 1963, 723. Ashley-Smith, J.; Green, M.; Stone, F. G. A. J. Chem. Soc. A 1969, 3019.
4. F; see, for example, the following: McBride, D. W.; Stafford, S. L.; Stone, F. G. A. J. Chem. Soc. 1963, 723. Ashley-Smith, J.; Green, M.; Stone, F. G. A. J. Chem. Soc. A 1969, 3019.
5. 2, isolated as the stable bis(trimethylphosphine) derivative by Firsich, D. W.; Lagow, R. J. J. Chem. Soc., Chem. Commun. 1981, 1283.
6. FI.
7. 3
8. (a) Hughes, R. Adv. Organomet. Chem. 1990, 31, 183.
9. (b) See, however: Yang, Z.-Y. J. Am. Chem. Soc. 1996, 118, 8140.
10. (a) See ref 4b for a discussion of difluorocarbene complexes with nickel and for leading references.
11. 5NiBr.
12. England et al. (England, D. C.; Solomon, L.; Krespan, C. G. J. Fluorine Chem. 1973, 3, 63) report the same observation in the synthesis of F-acryloyl fluoride with no indication of F-methylketene in equilibrium.
13. 3 with copper at elevated temperature (200 ̈C). Synthesis of acetylene 19 by dechlorination of 18 is also reported.
14. FZnI that imply an ordering of reactivities similar to ours.
15. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levein, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1988, 17, Supplement No. 1.
16. Chase, M. W., Jr.; Davies, C. A.; Downey, J. R., Jr.; Frurip, D. J.; McDonald, R. A.; Syverud, A. N. JANAF Thermochemical Tables, 3rd ed.; J. Phys. Chem. Ref. Data 1985, 14, Supplem 1.
17. Dixon, D. A.; Fukunaga, T.; Smart, B. E. J. Am. Chem. Soc. 1986, 108, 4027.
18. Dixon, D. A.; Farnham, W. B.; Heilemann, W.; Mews, R.; Noltemeyer, M. Heteroatom 1993, 4, 287.
19. Krespan, C. G.; Dixon, D. A. J. Fluorine Chem. 1996, 77, 117.
20. Wenthold, P. G.; Squires, R. R. J. Phys. Chem. 1995, 99, 2002.
21. (a) Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1983, 105, 2944.
22. (b) McMahon, T. B., private communication.
23. Dixon, D. A.; Smart, B. E. J. Phys. Chem. 1989, 93, 7772.