Bicyclo[1.1.1]pent-1-yl: A tertiary alkyl radical with enhanced reactivity

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 8059-8060

  Banks, Jeffrey T ^a   Ingold, Keith U ^a   Della, Ernest W ^a   Walton, John C ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CYCLOPENTANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030605107     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01825-4     Document Type: Article

References (28)

1. 1. Issued as N. R. C. C. No. 0000
2. 2. (a) NRCC
3. (b) NRCC Research Associate 1994-96
4. (c) Flinders University
5. (d) St Andrews University.
6. 3. Griller, D.; Ingold, K. U.; Krusic, P. J.; Fischer, H. J. Am. Chem. Soc., 1978, 100, 6750-6752.
7. 4. Walton, J. C. Chem, Soc. Rev., 1992, 21, 105-112.
8. 7.
9. 6. See for example, Fort, R. C.; Schleyer, P. v. R. J. Am. Chem. Soc., 1971, 93, 3189; Rüchardt, C. Angew. Chem. Int. Ed. Engl. 1970, 9, 830; Engel, P. S. Chem. Rev., 1980, 80, 99.
10. 6. See for example, Fort, R. C.; Schleyer, P. v. R. J. Am. Chem. Soc., 1971, 93, 3189; Rüchardt, C. Angew. Chem. Int. Ed. Engl. 1970, 9, 830; Engel, P. S. Chem. Rev., 1980, 80, 99.
11. 6. See for example, Fort, R. C.; Schleyer, P. v. R. J. Am. Chem. Soc., 1971, 93, 3189; Rüchardt, C. Angew. Chem. Int. Ed. Engl. 1970, 9, 830; Engel, P. S. Chem. Rev., 1980, 80, 99.
12. 7. Rüchardt, C.; Herwig, K.; Eichler, S. Tetrahedron Lett., 1969, 421; Giese, B. Tetrahedron Lwtt., 1979, 857; Giese, B.; Stellmach, J. Chem. Ber., 1980, 113, 3294.
13. 7. Rüchardt, C.; Herwig, K.; Eichler, S. Tetrahedron Lett., 1969, 421; Giese, B. Tetrahedron Lwtt., 1979, 857; Giese, B.; Stellmach, J. Chem. Ber., 1980, 113, 3294.
14. 7. Rüchardt, C.; Herwig, K.; Eichler, S. Tetrahedron Lett., 1969, 421; Giese, B. Tetrahedron Lwtt., 1979, 857; Giese, B.; Stellmach, J. Chem. Ber., 1980, 113, 3294.
15. 8. The tetrahedryl radical is even more "tied back" but will be unstable and has not been reported.
16. 9. Della, E. W.; Lochert, I. J. Org. Prep. Proc. Int., 1996, 28, 411-442.
17. 10. Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc., 1990, 112, 2194-2216.
18. 11. Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Am. Chem. Soc., 1991, 56, 307-316; Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc., 1992, 114, 601-620.
19. 11. Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Am. Chem. Soc., 1991, 56, 307-316; Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc., 1992, 114, 601-620.
20. 12. Delia, E. W.; Pigou, P. E.; Schiesser, C. H.; Taylor, D. K. J. Org. Chem. 1991, 56, 4659-4664.
21. 13. Rhodes, C. J.; Walton, J. C.; Delia, E. W. J. Chem. Soc., Perkin Trans. 2, 1993, 2125-2128.
22. 14. Griller, D.; Ingold, K. U.; Krusic, P. J.; Smart, B. E.; Wonchoba, E. R. J. Phys. Chem., 1982, 86, 1376-1377 and references cited.
23. 15. Adcock, W.; Binmore, G. T.; Krstic, A. R.; Walton, J. C.; Wilkie, J. J. Am. Chem. Soc., 1995, 117, 2758-2766.
24. 2), quat. C and CO too weak to detect.
25. 17. Della, E. W.; Taylor, D. K. Aust. J. Chem., 1991, 44, 881-885.
26. 18. Fischer, H. in Free Radicals in Biology and the Environment, Eds. Minisci, F.; Pedulli, G. F. Reidel, Dordrecht, 1996, in press.
27. 19 Paul, H.; Small, R. D. Jr.; Scaiano, J. C. J. Am. Chem. Soc., 1978, 100, 4520-4527.
28. 20. Hawari, J. A.; Engel, P. S.; Griller, D. Int. J. Chem. Kinet. 1985, 17, 1215-1219.