Chemistry Reference
In-Depth Information
C
(CH 2 ) n
C
O
C
C
136
137
1.14 Outlook
Originally the discovery of stable triarylmethyl radicals was mainly of theoretical interest and helped lay the
foundation for the electronic theory of organic chemistry. The realization of the existence of free radicals
with variable levels of stability then led to many advances in chemical theory and practical application,
as a variety of free radical reactions, such as polymerizations and substitutions, are of great industrial
importance. Similarly, free radicals have been found to play a vital role in biological processes. Now, with
the application of triaryl radicals in biology, these species are themselves of great utility, highlighting the
inextricable connection between fundamental knowledge and useful application.
Acknowledgements
Financial support by the Natural Sciences and Engineering Research Council of Canada is gratefully
appreciated.
References
1.
M. Gomberg, Ber. Dtsch. Chem. Ges ., 33 , 3150 -3163 (1900); J. Am. Chem. Soc ., 22 , 757 - 771 (1900).
2.
(a) J. C. Bailar, Jr., Biog. Mem. Nat. Acad. Sci. USA , 41 , 141 - 173 (1970). (b) C. S. Schoepfle and W. E.
Bachmann, J. Am. Chem. Soc ., 69 , 2921 -2925 (1947). (c) T. T. Tidwell, Chemical Intelligencer , July 2000,
33 - 38 (2000). (d) T. T. Tidwell, Adv. Phys. Org. Chem ., 36 , 1 - 58 (2001). (e) T. T. Tidwell, Angew. Chem. Int.
Ed ., 40 , 331 - 337 (2001). (g) G. B. Kaufman, Chem. Educator , 13 , 28 - 33 (2008). (h) N. M. Shishlov, Russ.
Chem. Rev , 75 , 863 - 884 (2006). (i) W. Schlenk, T. Weickel, and A. Herzenstein, Justus Liebigs Ann. Chem .,
372 , 1 - 20 (1910).
3.
(a) P. Jacobson, Ber. Dtsch. Chem. Ges ., 38 , 196 - 199 (1905). (b) E. Heintschel, Ber. Dtsch. Chem. Ges ., 36 ,
320 - 322 (1903). (c) E. Heintschel, Ber. Dtsch. Chem. Ges ., 36 , 579 (1903). (d) J. M. McBride, Tetrahedron ,
30 , 2009 -2022 (1974). (e) H. Lankamp, W. Th. Nauta, and C. MacLean, Tetrahedron Lett ., 9 , 249 - 254 (1968).
(f) L. Eberson, Chem. Intelligencer , 6 (3), 44 - 49 (2000).
4.
A. R. Forester, J. M. Hay, and R. H. Thomas, Organic Chemistry of Stable Free Radicals , Academic Press,
London, 1968.
5.
(a) J. Schmidlin, Ber. Dtsch. Chem. Ges ., 41 , 2471 - 2479 (1908). (b) E. G. Janzen, F. J. Johnston, and C. L.
Ay e r s , J. Am. Chem. Soc . 89 , 1176 -1183 (1967).
6.
(a) S.-H. Jang, P. Gopalan, J. E. Jackson, and B. Kahr, Angew. Chem. Int. Ed . 33 , 775 - 777 (1994). (b) B. Kahr,
J. E. Jackson, D. L. Ward, et al ., Acta Cryst. Sect. B 48 , 324 - 329 (1992).
7.
(a) H. Wieland, Ber. Dtsch. Chem. Ges ., 44 , 2550 - 2556 (1911). (b) D. E. Falvey, B. S. Khambatta, and G. B.
Schuster, J. Phys. Chem . 1990 , 94, 1056 - 1059. (c) K. U. Ingold, M. Smeu, and G. A. DiLabio, J. Org. Chem .,
71 , 9906 - 9908 (2006). (d) W. H. Urry and M. S. Kharasch, J. Am. Chem. Soc ., 66 , 1438 -1440 (1944). (e) P. H.
Kasai, D. McLeod, Jr., and H. C. McBay, J. Am. Chem. Soc ., 96 , 6864 -6868 (1974). (f) G. Brunton, H. C.
McBay, and K. U. Ingold, J. Am. Chem. Soc ., 99 , 4447 -4450 (1977).
(g) G. A. DiLabio, K. U. Ingold, S. Lin,
et al ., Angew. Chem. Int. Ed ., 49 , in press (2010).
Search WWH ::




Custom Search