Radical-chain addition of aldehydes to alkenes catalysed by thiols

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 1, 1998, Pages 67-75

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

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

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Indexed keywords

EID: 33748599312     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704878e     Document Type: Article

References (113)

1. (a) A. Ghosez, B. Giese and H. Zipse, in Methoden der Organischen Chemie (Houben-Weyl), ed. M. Regitze and B. Giese, Thieme, Stuttgart, 1989, vol. 1, ch. 9, pp. 690-697;
2. (b) D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 4, pp. 715, 779;
3. (c) C. Najera and M. Yus, Org. Prep. Proced. Int., 1995, 27, 383;
4. (d) D. Crich and H. Yuan, in Advances in Free-Radical Chemistry, ed. V. K. Rawal, JAI, Greenwich, 1998, vol. 2, in the press.
5. (a) D. L. Boger and R. J. Mathvink, J. Org. Chem., 1989, 54, 1777;
6. (b) D. L. Boger and R. J. Mathvink, J. Am. Chem. Soc., 1990, 112, 4003;
7. (c) D. L. Boger and R. J. Mathvink, J. Am. Chem. Soc., 1990, 112, 4008;
8. (d) D. L. Boger and R. J. Mathvink, J. Org. Chem., 1992, 57, 1429.
9. (a) D. Crich, C. Chen, J.-T. Hwang, H. Yuan, A. Papadatos and R. I. Walter. J. Am. Chem. Soc., 1994, 116, 8937;
10. (b) D. Crich and Q. Yao, J. Org. Chem., 1996, 61, 3566;
11. (c) D. Crich, K. A. Eustace, S. M. Fortt and T. J. Ritchie, Tetrahedron, 1990, 46, 2135;
12. (d) D. Batty and D. Crich, J. Chem. Soc., Perkin Trans. 1, 1992, 3193.
13. (a) C. E. Schwartz and D. P. Curran, J. Am. Chem. Soc., 1990, 112, 9272;
14. (b) D. P. Curran and H. Liu, J. Org. Chem., 1991, 56, 3463.
15. (a) M. P. Astley and G. Pattenden, Synlett, 1991, 335;
16. (b) L. Chen, G. B. Gill, G. Pattenden and H. Simonian, J. Chem. Soc., Perkin Trans. 1, 1996, 31.
17. M. Baliestri, C. Chatgilialoglu, N. Cardi and A. Sommazzi, Tetrahedron Lett., 1992, 33, 1787.
18. (a) D. J. Coveney, V. F. Patel and G. Pattenden, Tetrahedron Lett., 1987, 28, 5949;
19. (b) D. J. Coveney, V. F. Patel, G. Pattenden and D. M. Thompson, J. Chem. Soc., Perkin Trans. 1, 1990, 2721;
20. (c) V. F. Patel, G. Pattenden and D. M. Thompson, J. Chem. Soc., Perkin Trans. 1, 1990, 2729;
21. (d) G. Pattenden and S. J. Reynolds, Tetrahedron Lett., 1991, 32, 259;
22. (e) G. B. Gill, G. Pattenden and S. J. Reynolds, J. Chem. Soc., Perkin Trans. J, 1994, 369;
23. (f) G. Pattenden and S. J. Reynolds, J. Chem. Soc., Perkin Trans. 1, 1994, 379.
24. (a) J. Pfenninger, C. Heuberger and W. Graf, Helv. Chim. Acta, 1980, 63, 2328;
25. (b) D. Crich and S. M. Fortt, Tetrahedron, 1989, 45, 6581.
26. C. Chen, D. Crich and A. Papadatos, J. Am. Chem. Soc., 1992, 114, 8313.
27. F. Minisci and A. Citterio, Adv. Free-Radical Chem., 1980, 6, 65.
28. C. Walling, Free Radicals in Solution, Wiley, New York, 1957.
29. F. Jent, H. Paul, E. Roduner, M. Heming and H. Fischer, Int. J. Chem. Kinet., 1986, 18, 1113.
30. M. S. Kharasch, W. H. Urry and B. M. Kuderna, J. Org. Chem., 1949, 14, 248.
31. (a) T. M. Patrick, Jr., J. Org. Chem., 1952, 17, 1009;
32. (b) T. M. Patrick, Jr., J. Org. Chem., 1952, 17, 1269;
33. (c) J. D. LaZerte and R. J. Koshar, J. Am. Chem. Soc., 1955, 77, 910;
34. (d) H. Stockmann, J. Org. Chem., 1964, 29, 245;
35. (e) S. N. Lewis, J. J. Miller and S. Winstein, J. Org. Chem., 1972, 37, 1478;
36. (f) B. Fraser-Reid, R. C. Anderson, D. R. Hicks and D. L. Walker, Can. J. Chem., 1977, 55, 3986;
37. (g) P. Gottschalk and D. C. Neckers, J. Org. Chem., 1985, 50, 3498.
38. B. V. Rao, J. B. Chan, N. Moskowitz and B. Fraser-Reid, Bull. Soc. Chim. Fr., 1993, 130, 428.
39. (a) J.-P. Monthéard, C. R. Acad. Sci., Ser. C, 1965, 260, 577;
40. (b) J. A. Kampmeier, S. H. Harris and D. K. Wedegaertner, J. Org. Chem., 1980, 45, 315.
41. (a) R. Dulou, Y. Chretien-Bessiere and H. Desalbres, C. R. Acad. Sci., Ser. C, 1964, 258, 603;
42. (b) M. Julia, M. Maumy and L. Mion, Bull. Soc. Chim. Fr., 1967, 2641;
43. (c) M. Julia and M. Maumy, Bull. Soc. Chim. Fr., 1969, 2415, 2427;
44. (d) M. Chatzopoulos and J.-P. Monthéard, C. R. Acad. Sci., Ser. C, 1975, 280, 29.
45. (a) C. Walling and E. S. Huyser, Org. React., 1963, 13, 91;
46. (b) B. Giese, Radicals in Organic Synthesis: Formation of C-C Bonds, Pergamon, Oxford, 1986, ch. 3, pp. 72-73.
47. (a) B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2155;
48. (b) B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1996, 2719.
49. (a) E. F. P. Harris and W. A. Waters, Nature, 1952, 170, 212;
50. (b) K. E. J. Barrett and W. A. Waters, Discuss. Faraday Soc., 1953, 14, 221.
51. J. D. Berman, J. H. Stanley, W. V. Sherman and S. G. Cohen, J. Am. Chem. Soc., 1963, 85, 4010.
52. (a) V. Paul and B. P. Roberts, J. Chem. Soc., Chem. Commun., 1987, 1322;
53. (b) V. Paul and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1988, 1183;
54. (c) V. Paul, B. P. Roberts and C. A. S. Robinson, J. Chem. Res. (S), 1988, 264;
55. (d) V. Paul, B. P. Roberts and C. R. Willis, J. Chem. Soc., Perkin Trans. 2, 1989, 1953;
56. (e) H.-S. Dang and B. P. Roberts, Tetrahedron Lett., 1992, 33, 4621 (corrigendum p. 7070) and 6169;
57. (f) P. Kaushal, P. L. H. Mok and B. P. Roberts, J. Chem. Soc., Perkin Trans 2, 1990, 1663;
58. (g) H.-S. Dang and B. P. Roberts, J. Chem. Soc., Perkin Trans, 1, 1993, 891;
59. (h) P. L. H. Mok, B. P. Roberts and P. T. McKetty, J. Chem. Soc., Perkin Trans. 2, 1993, 665;
60. (i) H.-S. Dang, V. Diart and B. P. Roberts, J. Chem. Soc., Perkin Trans. 1, 1994, 1033;
61. (J) H.-S. Dang, V. Diart, B. P. Roberts and D. A. Tocher, J. Chem. Soc., Perkin Trans. 2, 1994, 1039.
62. (a) R. P. Allen, B. P. Roberts and C. R. Willis, J Chem. Soc., Chem. Commun., 1989, 1387;
63. (b) J. N. Kirwan, B. P. Roberts and C. R. Willis, Tetrahedron Lett., 1990, 31, 5093;
64. (c) S. J. Cole, J. N. Kirwan, B. P. Roberts and C. R. Willis, J. Chem. Soc., Perkin Trans, 1, 1991, 103;
65. (d) H.-S. Dang and B. P. Roberts, Tetrahedron Lett., 1995, 36, 2875;
66. (e) M. B. Haque and B. P. Roberts, Tetrahedron Lett., 1996, 37, 9123.
67. H.-S. Dang and B. P. Roberts, J. Chem. Soc., Chem. Commun., 1996, 2201.
68. (a) H. Kiefer and T. G. Traylor, Tetrahedron Lett., 1966, 6163;
69. (b) G. D. Mendenhall, Tetrahedron Lett., 1983, 24, 451;
70. (c) H.-T. E. Chen and G. D. Mendenhall, J. Am. Chem. Soc., 1984, 106, 6375;
71. (d) G. D. Mendenhall and H.-T. E. Chen, J. Phys. Chem., 1985, 89, 2849.
72. (a) K. Münger and H. Fischer, Int. J. Chem. Kinet., 1985, 17, 809;
73. (b) H. Fischer, in Substituent Effects in Radical Chemistry, ed. H. G. Viehe, Z. Janousek and R. Mérényi, Reidel, Dordrecht, 1986;
74. (c) A. Salikhov and H. Fischer, Appl. Magn. Reson., 1993, 5, 445;
75. (d) K. Hebergerand H. Fischer, Int. J. Chem. Kinet., 1993, 25, 913;
76. (e) J. Q. Wu and H. Fischer, Int. J. Chem. Kinet., 1995, 27, 167.
77. E. I. Miranda, M. J. Diaz, I. Rosado and J. A. Soderquist, Tetrahedron Lett., 1994, 35, 3221.
78. (a) Y. P. Tsentalovich and H. Fischer, J. Chem. Soc., Perkin Trans. 2, 1994, 729;
79. (b) A. Bakac and J. H. Espenson, J. Chem. Soc., Chem. Commun., 1991, 1497.
80. M. B. Haque and B. P. Roberts, unpublished results.
81. J. Berkowitz, G. B. Ellison and D. Gutman, J. Phys. Chem., 1994, 98, 2744.
82. Handbook of Chemistry and Physics, ed. D. R. Lide, CRC Press, Boca Raton, 75th edn., 1994-1995.
83. (a) Y.-D. Wu and D. K. W. Lai, J. Org. Chem., 1996, 61, 7904;
84. (b) F. G. Bordwell, X.-M. Zhang, A. V. Satish and J.-P. Cheng, J. Am. Chem. Soc., 1994, 116, 6605;
85. (c) E. M. Arnett and R. A. Flowers, II, Chem. Soc. Rev., 1993, 22, 9.
86. G. E. Carr, R. D. Chambers, T. F. Holmes and D. G. Parker, J. Organomet. Chem., 1987, 325, 13.
87. C. E. Brown, A. G. Neville, D. M. Rayner, K. U. Ingold and J. Lusztyk, Aust. J. Chem., 1995, 48, 363.
88. (a) C. Dean and D. Whittaker, J. Chem. Soc., Perkin Trans. 2, 1990, 1275;
89. (b) Y. Nakatani and K. Kawashima, Synthesis, 1978, 147;
90. (c) K. Sakai and O. Oda, Tetrahedron Lett., 1972, 4375.
91. Y. Cai and B. P. Roberts, unpublished results.
92. C. Chatgilialoglu, Chem. Rev., 1995, 95, 1229.
93. R. Schmid, M. Cereghetti, B. Heiser, P. Schonholzer and H.-J. Hansen, Helv. Chim. Acta, 1988, 71, 897.
94. H. O. House, D. S. Crumrine, A. Y. Teranishi and H. D. Olmstead, J. Am. Chem. Soc., 1973, 95, 3310.
95. W. Srisiri, A. B. Padias and H. K. Hall, J. Org. Chem., 1994, 59, 5424.
96. H. I. Jacobson, M. J. Griffin, S. Preis and E. V. Jensen, J. Am. Chem. Soc., 1957, 79, 2608.
97. (a) J. M. Joumier, J. Fournier, C. Bruneau and P. H. Dixneuf, J. Chem. Soc., Perkin Trans. 1, 1991, 3271;
98. (b) P. L. Gendre, T. Braun, C. Bruneau and P. H. Dixneuf, J. Org. Chem., 1996, 61, 8453.
99. H. Moorlag, J. G. de Vries, B. Kaptein, H. E. Schoemaker, J. Kamphuis and R. M. Kellogg, Rec. Trav. Chim. Pays-Bas, 1992, 111, 129.
100. L. A. Paquette, W. E. Fristad, D. S. Dime and T. R. Bailey, J. Org. Chem., 1980, 45, 3017.
101. R. Y. Levina, N. P. Shusherina, M. Y. Lurye and N. D. Orlova, Dokl. Chem. (Engl. Transl.), 1956, 106, 51.
102. (a) E. J. Cragoe, Jr. and A. M. Pietruszkiewicz, J. Org. Chem., 1957, 22, 1338;
103. (b) E. J. Cragoe, Jr., A. M. Pietruszkiewicz and C. M. Robb, J. Org. Chem., 1958, 23, 971.
104. D. T. Belmont and L. A. Paquette, J. Org. Chem., 1985, 50, 4102.
105. M. T. Begley, N. Housden, A. Johns and J. A. Murphy, Tetrahedron, 1991, 47, 8417.
106. K. Hiroi and H. Sato, Chem. Lett., 1986, 1723.
107. D. Batty and D. Crich, Synthesis, 1990, 273.
108. J. Tsuji, H. Nagashima and K. Hori, Tetrahedron Lett., 1982, 23, 2679.
109. G. Cauquis, B. Sillion and L. Verdet, Tetrahedron Lett., 1979, 3.
110. V. M. Shostakovskii, N. I. Shuikin and I. F. Bel'skii, Dokl. Chem. (Engl. Transl.), 1967, 176, 854.
111. S. Julia, M. Julia and L. Brasseur, Bull. Soc. Chim. Fr., 1962, 1634.
112. K. Saigo, H. Kurihara, H. Miura, A. Hongu, N. Kubato, H. Nohira and M. Hasegawa, Synth. Commun., 1984, 14, 787.
113. H. C. Brown and C. P. Garg, J. Am. Chem. Soc., 1961, 83, 2952.