72
C. Brule´, N. Hoffmann / Tetrahedron Letters 43 (2002) 69–72
7. For polarity effects in radical reactions, see: (a) Fischer,
Acknowledgements
H.; Radom, L. Angew. Chem. 2001, 113, 1380–1414;
Angew. Chem., Int. Ed. 2001, 40, 1340–1371; (b) Giese,
B.; Mehl, W. Tetrahedron Lett. 1991, 32, 4275–4278; (c)
Lefort, D.; Fossey, J.; Sorba, J. New J. Chem. 1992, 16,
219–232; (d) Tedder, J. M. Angew. Chem., Int. Ed. Engl.
1982, 21, 401–410.
The authors are grateful to Professor J. P. Pete for his
support and to Dr. Karen Ple´ (UMR 6013, CNRS) for
some language corrections of the manuscript.
8. Marinkovic´, S.; Hoffmann, N. Chem. Commun. 2001,
1576–1577.
References
9. For structure and stability of ketyl radicals, see: (a) Wu,
Y.-D.; Houk, K. N. J. Am. Chem. Soc. 1992, 114,
1656–1661; (b) Micheau, J. C.; Despax, B.; Paillous, N.;
Lattes, A.; Castellano, A.; Catteau, J. P.; Lablache-Com-
bier, A. Nouv. J. Chem. 1981, 5, 257–260; (c) Lloyd, R.
V.; Causey, J. G. J. Chem. Soc., Perkin Trans. 2 1981,
1143–1147; (d) Lloyd, R. V.; Causey, J. G.; Momany, F.
A. J. Am. Chem. Soc. 1980, 102, 2260–2263; (e) Gilbert,
B. C.; Trenwith, M. J. Chem. Soc., Perkin Trans. 2 1975,
1083–1090.
10. Hoffmann, N. Tetrahedron: Asymmetry 1994, 5, 879–886.
11. (a) Pfau, M.; Dulou, R.; Vilkas, M. Comptes Rendus
1962, 254, 1817–1818; (b) Horner, L.; Klaus, J. Liebigs
Ann. Chem. 1979, 1232–1257; (c) Vaßen, R.; Runsink, J.;
Scharf, H. D. Chem. Ber. 1986, 119, 3492–3497; (d)
Benko, Z.; Fraser-Reid, B.; Mariano, P. S.; Beckwith, A.
L. J. J. Org. Chem. 1988, 53, 2066–2072; (e) Fraser-Reid,
B.; Holder, N. L.; Hicks, D. R.; Walker, D. L. Can. J.
Chem. 1977, 55, 3978–3985; (f) Mann, J.; Weymouth-
Wilson, A. Carbohydrate Res. 1991, 216, 511–515; (g)
Fukunishi, K.; Inoue, Y.; Kishimoto, Y.; Mashio, F. J.
Org. Chem. 1975, 40, 628–632; for a recent example of a
similar addition of alkanes to electron deficient triple
bonds, see: (h) Garaghty, N. W.; Hannan, J. J. Tetra-
hedron Lett. 2001, 42, 3211–3213.
12. For a similar intramolecular reaction, see: (a) Belotti, D.;
Cossy, J.; Pete, J. P.; Portella, C. J. Org. Chem. 1986, 51,
4196–4200; (b) Cossy, J.; Madaci, A.; Pete, J. P. Tetra-
hedron Lett. 1994, 35, 1541–1544.
13. (a) Turro, N. J. Modern Molecular Photochemistry; Uni-
versity Science Books: Mill Valley, CA, 1991; (b) Mor-
ton, D. R.; Turro, N. J. In Advances in Photochemistry;
Pitts, J. N. Jr.; Hammond, G. S.; Gollnick, K., Eds.;
Wiley: New York, 1974; Vol. 9, pp. 197–309.
14. Dalton, J. C.; Snyder, J. J. J. Am. Chem. Soc. 1975, 97,
5192–5196.
15. For similar reactions see: (a) Cohen, S. G.; Green, B. J.
Am. Chem. Soc. 1969, 91, 6824–6829; (b) Kim, S. S.;
Mah, Y. J.; Kim, A. R. Tetrahedron Lett. 2001, 42,
8315–8317.
1. (a) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in
Organic Chemistry; Wiley: Chichester, 1995; (b) Giese, B.
Radicals in Organic Synthesis: Formation of Carbon–Car-
bon Bonds; Pergamon Press: Oxford, 1986; (c) Curran, D.
P. In Comprehensive Organic Synthesis; Trost, B. M.;
Fleming, I.; Semmelhack, M. F., Eds.; Pergamon Press:
Oxford, 1991; Vol. 4, pp. 715–777 and 779–831.
2. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of
Radical Reactions; VCH: Weinheim, 1996.
3. (a) Bertrand, S.; Hoffmann, N.; Pete, J. P. Eur. J. Org.
Chem. 2000, 2227–2238; (b) Bertrand, S.; Glapski, C.;
Hoffmann, N.; Pete, J. P. Tetrahedron Lett. 1999, 40,
3169–3172; (c) Bertrand, S.; Hoffmann, N.; Pete, J. P.
Tetrahedron Lett. 1999, 40, 3173–3174.
4. (a) Bertrand, S.; Hoffmann, N.; Humbel, S.; Pete, J. P. J.
Org. Chem. 2000, 65, 8690–8703; (b) Bertrand, S.; Hoff-
mann, N.; Pete, J. P.; Bulach, V. Chem. Commun. 1999,
2291–2292.
5. (a) Kavarnos, G. J. Fundamentals of Photoinduced Elec-
tron Transfer; VCH: New York, 1993; (b) Mattay, J.
Synthesis 1989, 233–252; (c) Mattay, J.; Vondenhof, M.
Topics in Current Chemistry (Photoinduced Electron
Transfer III), 1991; Vol. 159, pp. 219–255; (d) Albini, A.;
Fasani, E.; Mella, M. Topics in Current Chemistry (Pho-
toinduced Electron Transfer V), 1993; Vol. 168, pp. 143–
173; (e) Pandey, G. Topics in Current Chemistry
(Photoinduced Electron Transfer V), 1993; Vol. 168, pp.
175–221; (f) Lewis, F. In Advances in Electron Transfer
Chemistry; Mariano, P. S., Ed.; J.A.I. Press, 1996; Vol. 5,
pp. 1–39; (g) Cossy, J.; Pete, J. P. In Advances in Electron
Transfer Chemistry; Mariano, P. S. III, Ed.; J.A.I. Press,
1996; Vol. 5, pp. 141–195; (h) Yoon, U. C.; Mariano, P.
S.; Givens, R. S.; Atwater, B. W. III In Advances in
Electron Transfer Chemistry; Mariano, P. S., Ed.; J.A.I.
Press, 1994; Vol. 4, pp. 117–205; (i) Khim, S. K.; Ceder-
strom, E.; Ferri, D. C.; Mariano, P. S. Tetrahedron 1996,
52, 3195–3222; (j) Photoinduced Electron Transfer, Part A
to D; Fox, M. A.; Chanon, M., Eds.; Elsevier, 1988; (k)
Julliard, M.; Chanon, M. Chem. Rev. 1983, 83, 425–506;
(l) Pandey, G. Synlett 1992, 546–552.
6. Renaud, P.; Giraud, L. Synthesis 1996, 913–926.
.