Quantum Yields in the Photochemically Induced Radical Chemistry of Acyl Derivatives of Thiohydroxamic Acids

Journal of the American Chemical Society

Volumn 113, Issue 18, 1991, Pages 6937-6942

  Barton, Derek H R ^a   Blundell, Paul ^a   Jaszberenyi, Joseph C ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84878809664     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00018a034     Document Type: Article

References (105)

1. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Baldwin, J. E., Ser. Ed.; Pergamon Press: Oxford, 1986.
2. Ramaiah, M. Tetrahedron 1987, 43, 3541–3676.
3. Curran, D. P. Synthesis 1988, 417–439.
4. Curran, D. P. Synthesis 1988, 489–513.
5. Barton, D. H. R.; Zard, S. Z. Philos. Trans. R. Soc. London 1985, B311, 505–516.
6. Barton, D. H. R.; Zard, S. Z. Janssen Chim. Acta 1987, 4, 3–9.
7. Dauben, W. G.; Bridon, D. P.; Kowalczyk, B. A. J. Org. Chem. 1990, 55, 376–378.
8. Dauben, W. G.; Warshawsky, A. M. Org. Chem. 1990, 55, 3075–3087.
9. Dauben, W. G.; Kowalczyk, B. A.; Bridon, D. P. Tetrahedron Lett. 1989, 30, 2461–2464.
10. Dauben, W. G.; Wang, T.-Z.; Stephens, R. W. Tetrahedron Lett. 1990, 31, 2393–2396.
11. Dauben, W. G.; Cogen, J. M.; Behar, V. Tetrahedron Lett. 1990, 31, 3241–3244.
12. Zard, S. Z.; Forbes, J. E. J. Am. Chem. Soc. 1990, 112, 2034–2036.
13. Boivin, J.; Crépon, E.; Zard, S. Z. Tetrahedron Lett. 1991, 32, 199–202.
14. Porter, N. A.; Lacher, B.; Chang, V.H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309–8310.
15. Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H. G.; Lindner, H. J. J. Am. Chem. Soc. 1989, 111, 8311–8312.
16. Porter, N. A.; Kaplan, J. K.; Dussault, P. H. J. Am. Chem. Soc. 1990, 112, 1266–1267.
17. Porter, N. A.; Hogenkamp, D. J.; Khouri, F. F. J. Am. Chem. Soc. 1990, 112, 2402–2407.
18. Porter, N. A.; Swann, E.; Nally, J.; McPhail, A. T. J. Am. Chem. Soc. 1990, 112, 6740–6741.
19. Porter, N. E.; Wu, W.-X.; McPhail, A. T. Tetrahedron Lett. 1991, 32, 707–710.
20. Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1989, 111, 6265–6276.
21. Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872–8878.
22. Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896–898.
23. Curran, D. P.; van Elburg, P. A.; Giese, B.; Gilges, S. Tetrahedron Lett. 1990, 31, 2861–2864.
24. Jasperse, C. P.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 601–5609.
25. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738–6740.
26. Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272–9284.
27. Curran, D. P.; Seong, C. M. J. Am. Chem. Soc. 1990, 112, 9401–9403.
28. Curran, D. P. Synlett 1991, 63–72.
29. Barton, D. H. R.; Ozbalik, N. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 43, 349–366.
30. Barton, D. H. R. Aldrichim. Acta 1990, 23, 3–10.
31. Crich, D. Aldrichimica Acta 1987, 20, 35–42.
32. Barton, D. H. R.; Zard, S. Z. Pure Appl. Chem. 1986, 58, 675–684.
33. Barton, D. H. R.; Motherwell, W. B. Heterocycles 1984, 21, 1–19.
34. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc, Perkin Trans. 1 1975, 1574–1585.
35. Hartwig, W. Tetrahedron 1983, 39, 2609–2645.
36. Barton, D. H. R.; Motherwell, W. B.; Stange, A. Synthesis 1981, 743–745.
37. Barton, D. H. R.; Blundell, P.; Jaszberenyi, J.C. Tetrahedron, in press.
38. Barton, D. H. R.; Hartwig, W.; Hay-Motherwell, R. S.; Motherwell, W. B.; Stange, A. Tetrahedron Lett. 1982, 23, 2019–2122.
39. Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. J. Org. Chem. 1989, 54, 2217–2225.
40. Lin, T.-S.; Yang, J.-H.; Liu, M.-C.; Zhu, J.-L. Tetrahedron Lett. 1990, 31, 3829–3832.
41. Serafinowski, P. Synthesis 1990, 411–415.
42. Barrett, A. G. M.; Barton, D. H. R.; Bielski, R.; McCombie, S. W. J. Chem. Soc, Chem. Commun. 1977, 866–868.
43. Barrett, A. G. M.; Barton, D. H. R.; Bielski, R. J. Chem. Soc, Perkin Trans. 1 1979, 2378–2381.
44. Barton, D. H. R.; Zheng, D. K.; Gero, S. D. J. Carbohydr. Chem. 1982, 1, 105–108.
45. Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J.C. Tetrahedron Lett. 1991, 32, 2569–2572.
46. Robins, M. J.; Wilson, J. S. J. Am. Chem. Soc. 1981, 103, 932–933.
47. Robins, M. J.; Wilson, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 105, 4059–4065.
48. Barton, D. H. R.; Jaszberenyi, J.C. Tetrahedron Lett. 1989, 30, 2619–2622.
49. Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J.C. Tetrahedron Lett. 1990, 31, 3991–3994.
50. Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J.C. Tetrahedron Lett. 1990, 31, 4681–4684.
51. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413–1432.
52. Barton, D. H. R.; Crich, D.; Motherwell, W. B. J. Chem. Soc, Chem. Commun. 1983, 939–941.
53. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979–4982.
54. Barton, D. H. R.; Kretzschmar, G. Tetrahedron Lett. 1983, 24, 5889–5892.
55. Barton, D. H. R.; Crich, D.; Kretzschmar, G. Tetrahedron Lett. 1984, 25, 1055–1058.
56. Barton, D. H. R.; Crich, D.; Kretzschmar, G. J. Chem. Soc, Perkin Trans. 1 1986, 39–53.
57. Barton, D. H. R.; Togo, H.; Zard, S. Z. Tetrahedron 1985, 41, 5507–5516.
58. Barton, D. H. R.; Togo, H.; Zard, S. Z. Tetrahedron Lett. 1985, 26, 6349–6352.
59. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901–3924.
60. Barton, D. H. R.; Garcia, B.; Togo, H.; Zard, S. Z. Tetrahedron Lett. 1986, 1327–1330.
61. Barton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron 1986, 42, 2325–2328.
62. Barton, D. H. R.; Bridon, D.; Zard, S. Z. Tetrahedron Lett. 1986, 4309–4312.
63. Barton, D. H. R.; Crich, D. J. Chem. Soc, Perkin Trans. 1 1986, 1603–1611.
64. Barton, D. H. R.; Crich, D. J. Chem. Soc, Perkin Trans. 1 1986, 1613–1619.
65. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979–4982.
66. Barton, D. H. R.; Bridon, D.; Zard, S. Z. Tetrahedron Lett. 1984, 25, 5777–5780.
67. Newcomb, M.; Park, S. U.; Kaplan, J.; Marquardt, D. J. Tetrahedron Lett. 1985, 26, 5651–5654.
68. Newcomb, M.; Deeb, T. M. J. Am. Chem. Soc. 1987, 109, 3163–3165.
69. Newcomb, M.; Deeb, T. M.; Marquardt, D. J. Tetrahedron 1990, 46, 2317–2328.
70. Newcomb, M.; Marquardt, D. J.; Deeb, T. M. Tetrahedron 1990, 46, 2329–2344.
71. Newcomb, M.; Marquardt, D. J.; Kumar, M. U. Tetrahedron 1990, 46, 2345–2352.
72. Newcomb, M.; Kumar, M. U. Tetrahedron Lett. 1990, 31, 1675–1678.
73. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1988, 110, 4415–4416.
74. Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 111, 230–234.
75. Boivin, J.; Crépon, E.; Zard, S. Z. Tetrahedron Lett. 1990, 31, 6869–6872.
76. Newcomb, M.; Kumar, M. U.; Boivin, J.; Crépon, E.; Zard, S. Z. Tetrahedron Lett. 1991, 32, 45–48.
77. Beckwith, A. L. J.; Davison, I. G. E. Tetrahedron Lett. 1991, 32, 49–52.
78. Barton, D. H. R.; Jaszberenyi, J.C.; Morrell, A. I. Tetrahedron Lett. 1991, 32, 311–314.
79. Newcomb, M.; Park, S. U. J. Am. Chem. Soc. 1986, 108, 4132–4134.
80. Newcomb, M.; Kaplan, J. Tetrahedron Lett. 1987, 28, 1615–1618.
81. Bohne, C.; Boch, R.; Scaiano, J. C. J. Org. Chem. 1990, 55, 5414–5418.
82. Newcomb, M.; Weber, K. A. J. Org. Chem. 1991, 56, 1309–1313.
83. Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron 1988, 44, 3501–3512.
84. Barton, D. H. R.; Bridon, D.; Zard, S. Z. Heterocycles 1987, 25, 449–462.
85. Legrand, L. Bull. Soc. Chim. Fr. 1960, 337–343.
86. Clausen, K.; Lawesson, O.-S. Bull. Soc. Chim. Belg. 1979, 88, 305–311.
87. Legrand, L.; Lozac’h, N. Bull. Soc. Chim. Fr. 1961, 618–623.
88. Craine, L.; Raban, M. Chem. Rev. 1989, 89, 689–712.
89. Molina, P.; Arques, A.; Cartagena, I.; Valcarcel, M. V. Synth. Commun. 1985, 15, 643–648.
90. Legrand, L.; Lozach, N. Bull. Soc. Chim. Fr. 1963, 1161–1166.
91. Walter, W.; Vos, J. Liebigs Ann. Chem. 1966, 698, 113–121.
92. Calvert, J. G.; Pitts, J. N., Jr. Photochemistry; John Wiley & Sons: New York, 1967; pp 780–786.
93. Horspool, W. M. Aspects of Organic Photochemistry; Academic Press: London, 1976; pp 37–53.
94. Porter, G. B. Primary Process and Energy Transfer: Consistent Terms and Definitions. In Advances in Photochemistry; Pitts, J. N., Jr.; Hammond, G. S., Gollnick, K., Eds.; John Wiley & Sons: New York, 1974; Vol. 9, pp 147–196.
95. Mbarton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron Lett. 1985, 26, 593, 5942.
96. Barton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron 1987, 43, 4321–4328.
97. Barton, D. H. R.; Ramesh, M. Tetrahedron Lett. 1990, 31, 949–952.
98. Barton, D. H. R.; Boivin, J.; Sarma, J.; Silva, E.; Zard, S. Z. Tetrahedron Lett. 1989, 30, 4237–4240.
99. Barton, D. H. R.; Zard, S. Z.; Castagnino, E.; Corsano, S. Tetrahedron Lett. 1986, 27, 6337–6338.
100. Wessely, F.; Sinwel, F. Monatsh. Chem. 1950, 81, 1055–1070.
101. Wessely, F.; Schinzel, E. Monatsh. Chem. 1953, 84, 425.
102. Barton, D. H. R.; Quinkert, G. J. Chem. Soc. 1960, 1–9.
103. Quinkert, G. Angew. Chem., Int. Ed. Engl. 1972, 11, 1072–1087.
104. Quinkert, G.; Kleiner, E.; Freitag, B. J.; Glenneberg, J.; Billhardt, U.-M.; Chech, F.; Schmeider, K. R.; Schudok, C.; Steinmetzer, H. C.; Bats, J. W.; Zimmermann, G.; Durner, G.; Rehm, P.; Paulus, E. F. Helv. Chim. Acta 1986, 69, 469–537.
105. Quinkert, G. Pure Appl. Chem. 1973, 33, 285–316.