Radical-chain reactions of sulfonyl azides and of ethyl azidoformate with allylstannanes: Homolytic allylation at nitrogen

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 13, 1996, Pages 1493-1498

  Dang, Hai Shan ^a   Roberts, Brian P ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748631569     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001493     Document Type: Article

References (60)

1. B. P. Roberts and J. N. Winter, J. Chem. Soc., Perkin Trans. 2, 1979, 1353.
2. R. A. Abramovitch and E. P. Kyba, in The Chemistry of the Azido Group, ed. S. Patai, Interscience, New York, 1971, ch. 5.
3. L. Horner and G. Bauer, Tetrahedron Lett., 1966, 3573.
4. J. C. Brand and B. P. Roberts, J. Chem. Soc., Chem. Commun., 1981, 748;
5. J. Chem. Soc., Perkin Trans. 2, 1982, 1459.
6. J. E. Leffler and H. H. Gibson, Jr., J. Am. Chem. Soc., 1968, 90, 4117.
7. L. Benati, P. C. Montevecchi and P. Spagnolo, Tetrahedron Lett., 1978, 815;
8. L. Benati and P. C. Montevecchi, J. Org. Chem., 1981, 46, 4570.
9. S. Kim, G. H. Joe and J. Y. Do, J. Am. Chem. Soc., 1994, 116, 5521.
10. M. Frankel, D. Wagner, D. Gertner and A. Zilka, J. Organomet. Chem., 1967, 2, 518.
11. H. Redlich and W. Roy, Liebigs Ann. Chem., 1981, 1215.
12. S. Kim, G. H. Joe and J. Y. Do, J. Am. Chem. Soc., 1993, 115, 3328.
13. S. Kim and J. Y. Do, J. Chem. Soc., Chem. Commun., 1995, 1607.
14. S. Kim, K. S. Yoon, S. S. Kim and H. S. Seo, Tetrahedron, 1995, 51, 8437.
15. M. F. Sloan, W. B. Renfrow and D. S. Breslow, Tetrahedron Lett., 1964, 2905;
16. D. S. Breslow, M. F. Sloan, N. R. Newburg and W. B. Renfrow. J. Am. Chem. Soc., 1969, 91, 2273;
17. R. A. Abramovitch and W. D. Holcomb, J. Chem. Soc., Chem. Commun., 1969, 1298.
18. H.-S. Dang and B. P. Roberts, J. Chem. Soc., Perkin Trans, 1, 1996, 769.
19. G. E. Keck and J. B. Yates, J. Am. Chem. Soc., 1982, 102, 5289;
20. G. E. Keck, E. J. Erholm, J. B. Yates and M. R. Wiley, Tetrahedron, 1985, 41, 4079.
21. D. P. Curran, Synthesis, 1988, 489.
22. W. B. Motherwell and D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992, pp. 202-207.
23. Y. Yamamoto and N. Asoa, Chem. Rev., 1993, 93, 2207.
24. G. A. Russell and L. L. Herold, J. Org. Chem., 1985, 50, 1037.
25. G. Somer and J. B. F. N. Engberts, Tetrahedron Lett., 1977, 3901;
26. H. Teeninga and J. B. F. N. Engberts, J. Org. Chem., 1979, 44, 4717;
27. W. C. Danen and R. W. Gellert, J. Am. Chem. Soc., 1979, 102, 3264;
28. R. Sutcliffe, M. Anpo, A. Stolow and K. U. Ingold, J. Am. Chem. Soc., 1982, 104, 6064.
29. B. P. Roberts and J. N. Winter, J. Chem. Soc., Chem. Commun., 1978, 545;
30. J. C. Brand, B. P. Roberts and J. N. Winter, J. Chem. Soc., Perkin Trans. 2., 1983, 261,
31. M. D. Cook, B. P. Roberts and K. Singh, J. Chem. Soc., Perkin Trans. 2, 1983, 635.
32. J. C. Brand, M. D. Cook and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1984, 1187.
33. H.-S. Dang and A. G. Davies, J. Chem. Soc., Perkin Trans. 2, 1991, 2011;
34. J. Organomet. Chem., 1992, 430, 287.
35. B. C. Ranu, A. Sarkar and R. Chakraborty, J. Org. Chem., 1994, 59, 4114.
36. P. Frøyen, Phosphorus, Sulfur Silicon Relat. Elem., 1993, 78, 161.
37. M. Regitze, J. Hooker and A. Liedhegener, Org. Synth., 1973, Coll. Vol. 5, 179.
38. J. E. Leffler and Y. Tsuno, J. Org. Chem., 1963, 28, 902;
39. M. T. Reagan and A. Nickon, J. Am. Chem. Soc., 1968, 90, 4096.
40. D. L. Rector and R. E. Harmon, J. Org. Chem., 1966, 31, 2837.
41. L. Horner and A. Christmann, Chem. Ber., 1963, 96, 388.
42. C. Garganta, J. Hazelett and J. M. Shaw, Biochem. Biophys. Acta, 1985, 812, 261;
43. R. M. Moriarty and M. Rahman, J. Am. Chem. Soc., 1966, 88, 842.
44. S. M. Kumar, Synth. Commun., 1987, 17, 1015.
45. A. J. Hurbert, A. Ferson, G. Goebbels, R. Warin and P. Teyssié, J. Chem. Soc., Perkin Trans. 2, 1977, 11.
46. N. M. Sanghavi, V. L. Parab; B. S. Patravale and M. N. Patel, Synth. Commun., 1989, 19, 1499.
47. A. Fabrycy, J. Kaszubska, W. Jacobson and M. Gwiazda, Pr. Inst. Przem. Org., 1973, 5, 223
48. (Chem. Abstr., 1975, 83, 192957a).
49. J. Petranek and M. Večeřa, Collect. Czech. Chem. Commun., 1959, 24, 2191.
50. J. Dunogués and R. Calas, Synthesis, 1977, 469.
51. J. Wildeman and A. M. van Leusen, Synthesis, 1979, 733.
52. K. H. Bell, J. Chem. Soc., Perkin Trans, 1, 1988, 1957.
53. B. D. Gupta, S. Roy and S. Sen, Indian J. Chem., Sect. B, 1985, 24, 1032.
54. M. Ludwig, O. Pytela, K. Kalfus and M. Večeřa, Collect. Czech. Chem. Commun., 1984, 49, 1184.
55. M. S. Kharasch and R. A. Mosher, J. Org. Chem., 1952, 17, 453.
56. T. Kataoka, M. Yoshimatsu, Y. Noda, T. Sato, H. Shimizu and M. Hori, J. Chem. Soc., Perkin Trans. 1, 1993, 121.
57. J. K. Crandall and C. Pradat, J. Org. Chem., 1985, 50, 1327.
58. S. P. McManus and J. T. Carroll, J. Org. Chem., 1970, 35, 3768.
59. J. L. Brewbaker and H. Hart, J. Am. Chem. Soc., 1969, 91, 711;
60. E. Kleinpeter, R. Widera and M. Mühlstädt, Z. Chem., 1977, 17, 267.