Chromyl Complexes in the Direct Epoxidation of Alkenes

Journal of the American Chemical Society

Volumn 105, Issue 8, 1983, Pages 2368-2378

  Miyaura, N ^a   Kochi, J K ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344148006     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00346a044     Document Type: Article

References (95)

1. Beattie, J.K.; Haight, G.P.; Jr. Inorg. React. Mech. 1972, 17 (II), 93.
2. Wiberg, K.B. “Oxidation in Organic Chemistry”, Part A.; Academic Press: New York, 1965.
3. Trahanovsky, W.S. Methods Free-Radical Chem. 1973, 4, 133.
4. Freeman, F. Rev. React. Species Chem. React. 1973, 1, 37.
5. Cf. Cotton, F.A.; Wilkinson, G. “Advanced Inorganic Chemistry”, 4th ed.; Wiley: New York, 1980, p. 719 ff.
6. Berti, G. “Topics in Stereochemistry”; Allinger, N.L., Eliel, E.L., Eds.; Wiley: New York, 1973; Vol. 7. Sheldon, R.A.; Kochi, J.K. “Metal Catalyzed Oxidation of Organic Compounds”; Academic Press: New York, 1981.
7. Rappe, A.K.; Goddard, W.A., III J. Am. Chem. Soc. 1982, 104, 3287.
8. Mosher, W.A.; Steffgen, F.W.; Lansbury, P.T. J. Org. Chem. 1961, 26, 670.
9. Gatzke, A.L.; Stairs, R.A.; Diaper, D.G.M. Can. J. Chem. 1968, 46, 3695.
10. Gooden, R.; Brauman, J.I. J. Am. Chem. Soc. 1982, 104, 1483.
11. Rocek, J.; Drozd, J.C. J. Am. Chem. Soc. 1970, 92, 6668.
12. Poos, G.I.; Arth, G.E.; Beyler, R.E.; Sarrett, L.H. J. Am. Chem. Soc. 1953, 75, 425.
13. Collins, J.C.; Hess, W.W.; Frank, F.J. Tetrahedron. Leu. 1968, 3363.
14. Ellis, B.; Petrow, V. J. Chem. Soc. 1956, 4417.
15. Warrener, R.N.; Lee, T.S.; Russell, R.A.; Paddon-Row, M.N. Aust. J. Chem. 1978, 31, 1113.
16. Sundararaman, P.; Herz, W. J. Org. Chem. 1977, 42, 813.
17. Kalsi, P.S.; Kumar, K.S.; Wadia, M.S. Chem. Ind. (London) 1971, 31.
18. Usually a complex mixture resulting from allylic attack is obtained. See Dauben, W.G.; Lorber, M.; Fullerton, D.S.J. Org. Chem. 1969, 34, 3587.
19. Marshall, C.W.; Ray, R.E.; Laos, I.; Riegel, B. J. Am. Chem. Soc. 1957, 79, 6308.
20. Mailloux, M.; Weinman, J.; Weinman, S. Bull. Soc. Chim. Fr. 1970, 3627.
21. Rao, P.N.; Kurath, P. J. Am. Chem. Soc. 1956, 78, 5660.
22. Chromyl acetate has been obtained as a low-melting red solid [Krauss, H.L. Angew. Chem. 1958, 70, 502]. More commonly it is generated in situ from chromium trioxide and acetic anhydride.
23. Hickinbottom, W.J.; Hogg, D.R.; Peter, D.; Wood, D.G.M. J. Chem. Soc. 1954, 4400.
24. Hickinbottom, W.J.; Peter, D.; Wood, D.G.M. J. Chem. Soc. 1955, 1360.
25. Hickinbottom, W.J.; Moussa, G.E.M. J. Am. Chem. Soc. 1957, 4195.
26. Davis, M.A.; Hickinbottom, W.J. J. Chem. Soc. 1958, 2205.
27. Moussa, G.E.M.; Eweiss, N.F. J. Appl. Chem. 1969, 19, 313.
28. Bachelor, F.W.; Cheriyan, U.O.J. Chem. Soc, Chem. Commun. 1973, 195.
29. Bachelor, F.W.; Cheriyan, U.O. Can. J. Chem. 1976, 54, 3383.
30. Sharpless, K.B.; Teranishi, A.Y.; Backvall, J.E. J. Am. Chem. Soc. 1977, 99, 3120.
31. Barrett, A.G.M.; Barton, D.H.R.; Tsushima, T. J. Chem. Soc, Perkin Trans. 1 1980, 639.
32. Brown, S.D.; Gard, G.L. Inorg. Chem. 1973, 12, 483.
33. Harris, A.D.; Trebellas, J.C.; Jonassen, H.B. Inorg. Syn. 1967, 9, 83.
34. See also Schmeisser, M.; Lutzow, D. Angew. Chem. 1954, 66, 230.
35. For example, see ref 15b for styrene Oxidation. Oxidation of steroidal dienes by chromic acid gives enediols [Fieser, L.F.; Herz, J.E.; Huang, W.Y. J. Am. Chem. Soc. 1951, 73, 2397.
36. Fieser, L.F.; Huang, W.Y.; Babcock, J.E. J. Am. Chem. Soc. 1953, 75, 116.
37. Fieser, L.F.; Herz, J.E. J. Am. Chem. Soc. 1953, 75, 121.
38. Windaus, A. Chem. Ber. 1906, 39, 2249
39. Hickinbottom, W.J.; Wood, D.G.M. J. Chem. Soc. 1957, 1600
40. Bachelor, F.W.; Cheriyan, U.O. Tetrahedron Lett. 1973, 3291.
41. Kruse, W.J. Chem. Soc, Chem. Commun. 1968, 1610.
42. Groves, J.T.; Kruper, W. J., Jr. J. Am. Chem. Soc. 1979, 101, 7613.
43. Groves, J.T.; Kruper, W.J.; Nemo, T.E.; Myers, R.S. J. Mol. Cata. 1980, 7, 169.
44. For the oxochromium(IV) analogues, see Buchler, J.W.; Lay, K.L.; Castle, L.; Ullrich, V. Inorg. Chem. 1982, 21, 842.
45. Cf. Bersin, T.; Willfang, G. Chem. Ber. 1937, 70B, 2167.
46. Willfang, G. Chem. Ber. 1941, 74B, 145.
47. For example, the ability of solvents to coordinate to a metal center such as SbCl; is in the order: HMPA > py > DMF > DMK > MeCN > MeNO2 > CH2C12. See Gutman, V. “Coordination Chemistry in Nonaqueous Solutions”; Springer Verlag: New York, 1968.
48. The relative reactivity determined by the competition method relates to the disappearance of alkene and is probably comparable to that usually measured spectroscopically by the disappearance of chromium(VI). Compare the methods employed in ref 49-51.
49. Note that the epoxide of diadamantilidene was especially persistent since it is not susceptible to either electrophilic or nucleophilic ring opening: Wynberg, H.; Boelema, E.; Wieringa, J.H.; Strating, J. Tetrahedron. Leu. 1970, 3613.
50. Kon, H. J. Inorg. Nucl. Chem. 1963, 25, 933.
51. Krumpolc, M.; DeBoer, B.G.; Rocek, J. J. Am. Chem. Soc. 1978, 100, 145.
52. Wiberg, K.B.; Schafer, H. J. Am. Chem. Soc. 1969, 91, 933.
53. Freeman, F.; Armstead, C.R.; Essig, M.G.; Karchefski, E.M.; Kojima, C.J.; Manopoli, V.C.; Wickman, A.H.J. Chem. Soc, Chem. Commun. 1980, 65.
54. Jennette, K.W. J. Am. Chem. Soc. 1982 8 104, 874.
55. Krauss, H.L.; Leder, M.; Munster, G. Chem. Ber. 1963, 96, 3008.
56. Rocek, J.; Radkowsky, A.E. J. Am. Chem. Soc. 1968, 90, 2986.
57. Rocek, J.; Radkowsky, A.E. J. Am. Chem. Soc. 1973, 95, 7123.
58. Wiberg, K.B.; Mukherjee, S.K. J. Am. Chem. Soc. 1974, 96, 1884.
59. Wiberg, K.B.; Mukherjee, S.K. J. Am. Chem. Soc. 1974, 96. 6647.
60. Nave, P.M.; Trahanovsky, W.S. J. Am. Chem. Soc. 1970, 92, 1120.
61. Miteva, M.; Bonchev, P.; Kabasanov, K.; Petrov, G.; Natsokova, M. Dokl. Bolg. Akad. Nauk. 1978, 31, 1437.
62. However, compare studies of the electrochemical Oxidation of ketones by Becker, J.Y.; Byrd, L.R.; Miller, L.L.; So, Y.H. J. Am. Chem. Soc. 1975, 97, 853.
63. Becker, J.Y.; Miller, L.L.; Siegel, T.M. J. Am. Chem. Soc. 1975, 97, 849.
64. Kuznetsova, N.I.; Lik-holobov, V.A.; Fedotov, M.A.; Yermakov, Y.I., J. Chem. Soc, Chem. Commun. 1982, 973.
65. Awasthy, A.K.; Rocek, J. J. Am. Chem. Soc 1969, 91, 991.
66. Freeman, F.; Arledge, K.W. J. Org. Chem. 1972, 37, 2656.
67. Freeman, F.; Yamachika, N.J. J. Am. Chem. Soc. 1972, 94, 1214.
68. Dryuk, V.G. Tetrahedron 1976, 32, 2855, and Plesnicar, B.; Tasevski, M.; Azman, A.J. Am. Chem. Soc. 1978, 100, 743.
69. Freeman, F. Chem. Rev. 1975, 75, 439.
70. Cram, D.J.; Allinger, N.L. J. Am. Chem. Soc. 1956, 78, 2518.
71. Geluk, H.W. Synthesis 1970, 652.
72. Perrin, D.D.; Armarego, W.L.F.; Perrin, D.R. “Purification of Laboratory Chemicals”; Pergamon Press: New York, 1980.
73. Freeman, F.; Yamachika, N.J. J. Am. Chem. Soc. 1970, 92, 3730.
74. Sisler, H.H. Inorg. Syn. 1946, 2, 205.
75. Schildknecht, H.; Fottinger, W. Justus Liebigs Ann. Chem. 1962, 659, 20.
76. Furman, N.H. “Standard Methods of Chemical Analysis”, 6th ed.; Van Nostrand: Princeton, 1962; Vol. 1 p. 355.
77. Gerlach, J.N.; Gard, G.L. Inorg. Chem. 1970, 9, 1565.
78. Helmholz, U.; Brennan, H.; Wolfsberg, M. J. Chem. Phys. 1955, 23, 853.
79. Compare results by Brown, S.D., and Gard, G.L., in ref 20.
80. Swern, D. Org. React. 1953, 7, 378.
81. Swern, D.; Billen, G.N.; Scanlan, J.T. J. Am. Chem. Soc. 1946, 68, 1504.
82. Crandall, J.K. J. Org. Chem. 1964, 29, 2830.
83. King, L.F. J. Am. Chem. Soc. 1939, 61, 2383.
84. Levy, J.; Dvoleitzka-Combinska, M. Bull. Soc. Chim. Fr. 1931, 49, 1765.
85. Lynch, B.M.; Pausacker, K.H. J. Chem. Soc. 1955, 1525.
86. See, e.g., Roebuck, A.; Adkins, H. Org. Syn. 1955, 3, 217.
87. Coffey, S. “Rodd's Chemistry of Carbon Compounds”; Elsevier: New York, 1965; Vol. I.D.
88. King, A. Ann. Chim. Phys. 1905, 5 [8], 557.
89. Grignard, V. Ann. Chim. Phys. 1907, 10 [8], 31.
90. Tiffenau, M. Ann. Chim. Phys. 1907, 10 [8], 344.
91. Movsumzade, M.M.; Kerimova, N.G.; Shabanov, A.L. Azer. Khim. Zh. 1968, 116;
92. Movsumzade, M.M.; Kerimova, N.G.; Shabanov, A.L., Chem. Abstr. 1969, 71, 124297n.
93. Levy, J.; Dvoleitzka-Combinska, M. Bull. Soc. Chim. Fr. 1937, 60, 1060.
94. Kon, H. Bull. Chem. Soc. Jpn. 1962, 35, 2054.
95. Garifyanov, N.S.; Kozyrev, B.M.; Fedofov, V.N. Dokl. Akad. Nauk SSSR 1968, 77, 808.