Carbon-carbon bond formation by radical addition-fragmentation reactions of O-tert-alkyl enols and O-cyclopropylcarbinyl enols

Tetrahedron Letters

Volumn 44, Issue 25, 2003, Pages 4645-4648

  Cai, Yudong ^a   Roberts, Brian P ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Addition reactions; Alkylation; Fragmentation reactions; Radicals and radical reactions

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ALKYL GROUP; CARBON; CARBONYL DERIVATIVE;

ADDITION REACTION; ALKYLATION; ALLYLATION; ARTICLE; CHEMICAL BINDING; FRAGMENTATION REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION;

EID: 0038440722     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01092-X     Document Type: Article

References (34)

1. Rosenstein, I. J. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P. Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, Chapter 1.4, pp. 50-71.
2. Motherwell W.B., Crich D. Free Radical Chain Reactions in Organic Synthesis. 1992;Academic Press, London.
3. Colombani D., Chaumont P. Prog. Polym. Sci. 21:1996;439-503.
4. Colombani D., Chaumont P. Acta Polym. 49:1998;225-231.
5. Colombani D. Prog. Polym. Sci. 24:1999;425-480.
6. Meijs G.F., Rizzardo E. Makromol. Chem. Rapid Commun. 9:1988;547-551 Rizzardo, E.; Meijs, G. F.; Thang, S. H. US Patent 6197905 (2001).
7. Claisen L. Chem. Ber. 29:1896;2931-2932.
8. Wiberg K.B., Rowland B.I. J. Am. Chem. Soc. 77:1955;1159-1163.
9. Wiberg K.B., Shryne T.M., Kinter R.R. J. Am. Chem. Soc. 79:1957;3160-3164.
10. Wiberg K.B., Kinter R.R., Motell E.L. J. Am. Chem. Soc. 85:1963;450-454.
11. Wang S., Morrow G.W., Swenton J.S. J. Org. Chem. 54:1989;5364-5371.
12. Perkins M.J., Roberts B.P. J. Chem. Soc., Perkin Trans. 2. 1975;77-84.
13. Dang H.-S., Franchi P., Roberts B.P. Chem. Commun. 2000;499-500.
14. Fielding A.J., Franchi P., Roberts B.P., Smits T.M. J. Chem. Soc., Perkin Trans. 2. 2002;155-163.
15. Dang H.-S., Roberts B.P. J. Chem. Soc., Perkin Trans. 1. 2002;1161-1170.
16. Cai Y., Dang H.-S., Roberts B.P. J. Chem. Soc., Perkin Trans. 1. 2002;2449-2458.
17. Roepel M.G. Tetrahedron Lett. 43:2002;1973-1976.
18. Laurencelle N., Pacey P.D. J. Am. Chem. Soc. 115:1993;625-631.
19. Harvey J.N., Viehe H.G. J. Prakt. Chem. 337:1995;253-265.
20. Luo Y.-R., Benson S.W. J. Phys. Chem. A. 101:1997;3042-3044.
21. CRC Handbook of Chemistry and Physics, 82nd ed.; CRC Press: Boca Raton, 2001.
22. t in THF (see Middleton, D. S.; Simpkins, N. S. Synth. Commun. 1989, 19, 21-29).
23. t in THF (see Middleton, D. S.; Simpkins, N. S. Synth. Commun. 1989, 19, 21-29).
24. 2C(O)Ph.
25. 2C(O)Ph (38%) and no 11b.
26. 5 requires C, 64.7; H, 6.5%. Satisfactory spectroscopic and analytical data were obtained for all new compounds described herein.
27. Fuentes J., Molina J.L., Pradera M.A. Tetrahedron: Asymmetry. 9:1998;2517-2532.
28. Wissner A., Grudzinskas C.V. J. Org. Chem. 43:1978;3972-3974.
29. Sakaitani M., Ohfune Y. J. Org. Chem. 55:1990;870-876.
30. Because of its higher boiling point, the vinyl ether 6d was used in preference to commercially available tert-butyl vinyl ether.
31. Roberts C., Walton J.C. Chem. Commun. 1984;1109-1111.
32. Bowry V.W., Lusztyk J., Ingold K.U. J. Am. Chem. Soc. 113:1991;5687-5698.
33. Beckwith A.L.J., Bowry V.W. J. Am. Chem. Soc. 116:1994;2710-2716.
34. For a related type of reaction that utilises O-stannyl enolates, see: Miura K., Fujisawa N., Saito H., Wang D., Hosomi A. Org. Lett. 3:2001;2591-2594.