The invention of radical reactions. Part XXXVII. A convenient radical synthesis of dialkyl diselenides from carboxylic acids

Tetrahedron

Volumn 52, Issue 34, 1996, Pages 11163-11176

  Barton, Derek H R ^a   Fontana, Giovanni ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SELENIDE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030593701     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00665-5     Document Type: Article

References (59)

1. 1) a) Part XXXV: Barton, D.H.R.; Fontana, G.; Yang, Y. Tetrahedron 1996, 52, 2705.
2. b) Part XXXVI: Barton, D.H.R.; Jaszberenyi, J.Cs.; Liu, W.; Shinada, T. Tetrahedron 1996, 52, 2717.
3. 2) For a comprehensive treatment of organoselenium chemistry see "Organoselenium Compounds: Their Chemistry and Biology", Klayman, D.L.; Günther, W.H.H., Wiley Ed., New York, NY 1973.
4. 3) For reviews: a) Reich, H.J. Acc. Chem. Res. 1979, 12, 22. b) Clive, D.L.J. Tetrahedron 1978, 34, 1048. c) Liotta, D. Acc. Chem. Res. 1984, 17, 28.
5. 3) For reviews: a) Reich, H.J. Acc. Chem. Res. 1979, 12, 22. b) Clive, D.L.J. Tetrahedron 1978, 34, 1048. c) Liotta, D. Acc. Chem. Res. 1984, 17, 28.
6. 3) For reviews: a) Reich, H.J. Acc. Chem. Res. 1979, 12, 22. b) Clive, D.L.J. Tetrahedron 1978, 34, 1048. c) Liotta, D. Acc. Chem. Res. 1984, 17, 28.
7. 4) a) Bergstrom, F.W. J. Am. Chem. Soc. 1926, 48, 146.
8. b) Bird, M.L.; Challenger, L. J. Chem. Soc. 1942, 570.
9. 5) Tschugaeff, L.; Chlopin, W. Chem. Ber. 1914, 47, 1269.
10. 6) a) Klayman, D.L.; Griffin, T.S. J. Am. Chem. Soc. 1973, 95, 197.
11. b) Gladysz, J.; Hornby, J.L.; Garbe, J.E. J. Org. Chem. 1978, 43, 1204.
12. c) Bergman, J.; Engman, L. Synthesis 1980, 7, 596.
13. 7) Clive, D.L.J.; Menchen, S.M. J. Org. Chem. 1979, 44, 4279.
14. 8) Syper, L.; Mlochowski, J. Synthesis 1984, 439.
15. 9) Wagner, G.; Nuhn, P. Arch. Pharm. (Weinheim) 1964, 297, 401.
16. 10) Günther, W.H.H.; Mautner, H.G: J. Am. Chem Soc. 1965, 87, 2708.
17. 11) Li, J.Q.; Bao, W.L.; Lue, P.; Zhan, X. Synth. Comm. 1991, 21 (6), 799.
18. 12) Lue, P.; Zhan, X. Synth. Comm. 1993, 23 (12), 1721.
19. 13) a) Ward, H.P.; O'Donnel, I.L. J. Am. Chem Soc. 1945, 67, 883.
20. b) Backer, H.J.; Hurenkamp, J.B.G. Recl. Trav. Chim. Pay-Bas. 1942, 61, 802.
21. 14) Günther, W.H.H. J. Org. Chem. 1967, 32, 3929.
22. 15) Jeu, K.Y.; Cava, M.P. J. Org. Chem. 1983, 48, 1449.
23. 16) Waitkins, G.R.; Shutt, R. Inorg. Synth. 1946, 2, 186.
24. 17) Hari, T.; Sharpless, K.B. J. Org. Chem. 1978, 43, 1689.
25. 18) a) Cohen, V.I. J. Org. Chem. 1977, 42, 2510.
26. b) Nishiyama, Y.; Hamanaka, S. Synth. Comm. 1986, 16, 1059.
27. 19) a) Barton, D.H.R.; Zard, S.Z. Pure Appl. Chem. 1986, 58, 675.
28. b) Idem, Janssen Chimica Acta 1987, 4, 3.
29. c) Barton, D.H.R. Aldrichimica Acta 1990, 23, 3.
30. d) Barton, D.H.R.; Chern, C.-Y.; Jaszberenyi, J.Cs. Aust. J. Chem. 1995, 48, 407.
31. e) Barton, D.H.R.; Crich, D.; Motherwell, W.B. J. Chem. Soc., Chem. Comm. 1983, 931.
32. f) Barton, D.H.R.; Crich, D.; Motherwell, W.B.Tetrahedron 1985, 41, 3901.
33. g) Newcomb, M.; Weber, K.A. J. Org. Chem. 1991, 56, 1309.
34. 20) Barton, D.H.R.; Zhu, J. J. Am. Chem. Soc. 1993, 115, 2071.
35. 21) Barton, D.H.R.; Castagnino, E.; Jaszberenyi, J.Cs. Tetrahedron Lett. 1994, 35, 6057.
36. 22) a) Richter, H.; Kulcke, W.; Specht, H.Z. Naturforsch 1952, 7a, 511.
37. b) Burbank, R.D. Acta Cryst. 1951, 4, 140.
38. c) ibid. 1952, 5, 236.
39. d) Bagnall, K.W. in Comprehensive Inorganic Chemistry 1973, Pergamon Press, New York, Ch. 24, p 940.
40. e) see ref. 2.
41. 23) Barton, D.H.R.; McCombie, S.W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
42. 24) a) Klayman, D.H.; Griffin, T.S. J. Am. Chem. Soc. 1973, 95, 197.
43. b) see ref. 2 and ref. 23.
44. 25) a) Jensen, K.A.; Nielsen, P.H. Acta Chem. Scand. 1966, 20, 597.
45. b) Ogawa, A.; Miyake, J; Kambe, N; Sonoda, N J. Bull. Chem. Soc. Jpn. 1985, 58, 1448.
46. c) Rae, I.D. Aust. J. Chem. 1979, 32, 567.
47. d) Cullen, E.R.; Guziec, F.S.; Murphy, C.J.; Wong, T.C. J. Chem. Soc., Perkin Trans. 2 1982, 4, 473.
48. 26) Harris, R.K.; Mann, B.E.; NMR and the Periodic Table, Academic Press, 1978, Ch. 12, p. 405 and references cited therein.
49. 27) Eggert, H.; Nielsen, O.; Henriksen, L. J. Am. Chem. Soc. 1986, 108(8), 1725.
50. 28) a) Barton, D.H.R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501.
51. b) Idem, ibid. 1988, 44, 7385.
52. 29) a) Higuchi, H.; Otsubo, T.; Oguna, F.; Yamaguchi, H.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1982, 55, 182.
53. b) Thompson, D.P.; Boudjouk, P. J. Org. Chem. 1988, 53, 2109.
54. c) Yoshimatsu, M.; Sato, T.; Shimizu, H.; Hori, M.; Kataoka, T. J. Org. Chem. 1994, 59, 1011.
55. d) Kataoka, T.; Ohe, Y.; Umeda, A.; Iwamura, T. Chem. Pharm. Bull. 1994, 42(4), 811.
56. 30) a) Sato, S.; Ogawa, T. Carbohydr. Res. 1987, 767, 197.
57. b) Pascal Langlois' thesis. Université de Paris Sud, September 15, 1989.
58. 31) see ref. 6b and ref. 18b.
59. 32) Palacios, S.M.; Santiago, A.N.; Rossi, R.A. J. Org. Chem. 1984, 49, 4609.