Mechanisms of hydrolysis and rearrangements of epoxides

Advances in Physical Organic Chemistry

Volumn 40, Issue , 2005, Pages 247-298

  Whalen, Dale L ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845948228     PISSN: 00653160     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-3160(05)40006-4     Document Type: Review

References (142)

1. Rosowsky, A. (1964). In Heterocyclic Compounds with Three- and Four-Membered Rings. Weissberber, A. (ed.), Part 1, pp. 1-523, Wiley-Interscience, New York
2. Buchanan, J.G. and Sable, H.Z. (1972). In Selective Organic Transformations, Thyagarajan, B.S. (ed.), vol. 2, pp. 1-95, Wiley-Interscience, New York
3. Cross A.D. Quart. Rev. 14 (1960) 317-335
4. Nicolaou D.C., and Smith A.L. Acc. Chem. Res. 25 (1992) 497-503
5. Bierl B.A., Beroza M., and Collier C.W. Science 170 (1970) 87-89
6. Persoons C.J., Verwiel P.E.J., Ritter F.J., Talman E., Nooijen P.J.F., and Nooigen W.J. Tetrahedron Lett. 24 (1976) 2055-2058
7. Dahm K.H., Trost B.M., and Roller H. J. Am. Chem. Soc. 89 (1967) 5292-5294
8. El Masri A.M., Smith J.N., and Williams R.T. J. Biochem. 68 (1958) 199-204
9. Boyland E., Ramsay G.S., and Sims P. J. Biochem. 78 (1961) 376-384
10. Wogan G.N. Cancer Res. 52 (1992) 2114-2118
11. Olson J.H., Dragsted L., and Autrup H. Br. J. Cancer, 58 (1988) 392-396
12. Hayes R.B., Van Nieuwenhuize J.P., Raatgever J.W., and ten Kate F.J.W. Food Chem. Toxicol. 22 (1984) 39-43
13. Ivers R.S., Coles B.F., Raney K.D., Thier R., Guengerich F.P., and Harris T.M. J. Am. Chem. Soc. 116 (1994) 1603-1609
14. Dipple, A., Moschel, R.C. and Bigger, C.A.H. (1984). In Chemical Carcinogens, Searle, C.E. (ed.) (2nd edn), vol. 1, ACS Monograph 182, pp. 41-163. American Chemical Society, Washington, DC
15. Harvey, R.G. (ed.) (1985) Polycyclic hydrocarbons and carcinogenesis, ACS Symposium Series 283. American Chemical Society, Washington, DC
16. Thakker D.R., Yagi H., Akagi H., Koreeda M., Lu A.Y.H., Levin W., Wood A.W., Conney A.H., and Jerina D.M. Chem. Biol. Interact. 16 (1977) 281-300
17. For historical reviews, see (a) Phillips, D.H. (1983). Nature 303, 468-472; (b) Rubin, H. (2001). Carcinogenesis 22, 1903-1930
18. Luch A., Platt K.L., and Seidel A. Carcinogenesis 19 (1998) 639-648
19. Greenberg, A. and Liebman, J.F. (1978). Strained Organic Molecules, p. 281. Academic Press, New York
20. Sawicka D., Wilsey S., and Houk K.N. J. Am. Chem. Soc. 121 (1999) 864-865
21. Wolk J.L., Sprecher M., Basch H., and Hoz S. Org. Biomol. Chem. 2 (2004) 1065-1069
22. Brønsted J.N., Kilpatrick M., and Kilpatrick M. J. Am. Chem. Soc. 51 (1929) 428-461
23. Long F.A., and Pritchard J.G. J. Am. Chem. Soc. 78 (1956) 2663-2667
24. Long F.A., and Pritchard J.G. J. Am. Chem. Soc. 78 (1956) 2667-2670
25. Bunnett J.F. J. Am. Chem. Soc. 83 (1961) 4956-4967
26. Bunnett J.F. J. Am. Chem. Soc. 83 (1961) 4968-4973
27. Bunnett J.F. J. Am. Chem. Soc. 83 (1961) 4973-4977
28. Bunnett J.F. J. Am. Chem. Soc. 83 (1961) 4978-4983
29. Bunnett J.F., and Olsen F.P. Can. J. Chem. 44 (1966) 1899-1916
30. Grunwald E., Heller A., and Klein F.S. J. Chem. Soc. (1957) 2604-2613
31. Wohl R.A. Chimia 28 (1974) 1-5
32. Toteva M.M., and Richard J.P. J. Am. Chem. Soc. 118 (1996) 11434-11445
33. Billing, G.D. and Mikkelsen, K.V. (1996). Molecular Dynamics and Chemical Kinetics, p. 108, Wiley, New York; (b) Castner Jr., E.W., Maroncelli, M. and Fleming, R. (1987). J. Chem. Phys. 86, 1090-1097
34. Richard J.P. J. Org. Chem. 57 (1992) 625-629
35. Pritchard, J.G. and Siddiqui, I.A. (1973). J. Chem. Soc. Perk. II, 452-457
36. Archer I.V.J., Leak D.J., and Widdowson D.A. Tetrahedron Lett. 37 (1996) 8819-8822
37. Henbest, H.B., Smith, M. and Thomas, A. (1958). J. Chem. Soc. 3293-3298
38. Parker R.E., and Isaacs N.S. Chem. Rev. 59 (1959) 737-799
39. Data were taken from Streitwieser, A. (1962). Solvolytic Displacement Reactions, p. 12. McGraw-Hill, New York
40. Whalen D.L. J. Am. Chem. Soc. 95 (1973) 3432-3434
41. Whalen D.L., and Ross A.M. J. Am. Chem. Soc. 96 (1974) 3678-3679
42. Ross A.M., Pohl T.M., Piazza K., Thomas M., Fox B., and Whalen D.L. J. Am. Chem. Soc. 104 (1982) 1658-1665
43. Bartlett P.D., and Ross S.D. J. Am. Chem. Soc. 70 (1948) 926-929
44. Kadesch R.G. J. Am. Chem. Soc. 68 (1946) 41-45
45. DeWolfe R.H., and Young W.G. Chem. Rev. 56 (1956) 753-901
46. Anet F.A., and Yavari I. J. Am. Chem. Soc. 100 (1978) 7817-7819
47. Audier H.E., Dupin J.F., and Jullien J. Bull. Soc. Chim. Fr. 9 (1968) 3850-3856
48. Hanzlik R.P., and Westkaemper R.B. J. Am. Chem. Soc. 102 (1980) 2464-2467
49. Jacober S.P., and Hanzlik R.P. J. Am. Chem. Soc. 108 (1986) 1594-1597
50. Blumenstein J.J., Ukachukwu V.C., Mohan R.S., and Whalen D.L. J. Org. Chem. 58 (1993) 924-932
51. Biggs J., Chapman N.B., Finch A.F., and Wray V. J. Chem. Soc. B (1971) 55-63
52. Richard J.P., Rothenberg M.E., and Jencks W.P. J. Am. Chem. Soc. 106 (1984) 1361-1372
53. Tsuno Y., Kusuyama Y., Sawada M., Fuji T., and Jukawa Y. Bull. Soc. Chem. Jpn. 48 1 (1975) 3337-3346
54. Richard J.P., and Jencks W.P. J. Am. Chem. Soc. 106 (1984) 1383-1396
55. Berti G., Bottari F., Ferrarini P.L., and Macchia B. J. Org. Chem. 30 (1965) 4091-4096
56. Dupin C., and Dupin J.-F. Bull. Soc. Chim. Fr. 11 (1970) 249-251
57. Lin B., and Whalen D.L. J. Org. Chem. 59 (1994) 1638-1641
58. Biggs, J., Chapman, N.B. and Wray, V. (1971). J. Chem. Soc. B 71-74
59. Whalen, D.L., unpublished results
60. Richard J.P., and Jencks W.P. J. Am. Chem. Soc. 104 (1982) 4689-4691
61. Audier H.E., Dupin J.F., and Jullien J. Bull. Soc. Chim. Fr. 7 (1966) 2811-2816
62. Audier H.E., Dupin J.F., and Jullien J. Bull. Soc. Chim. Fr. 9 (1968) 3850-3855
63. Mohan R.S., and Whalen D.L. J. Org. Chem. 58 (1993) 2663-2669
64. Laird R.M., and Parker R.E. J. Am. Chem. Soc. 83 (1961) 4277-4281
65. Audier H.E., Dupin J.F., and Jullien J. Bull. Soc. Chim. Fr. 9 (1968) 3844-3850
66. Battistini C., Balsamo A., Berti G., Crotti P., Macchia B., and Macchia F. J. Chem. Soc. Chem. Commun. (1974) 712-713
67. Battistini C., Crotti P., Donatella D., and Macchia F. J. Org. Chem. 44 (1979) 1643-1647
68. Crotti P., Dell'Omodarme G., Ferretti M., and Macchia F. J. Am. Chem. Soc. 109 (1987) 1463-1469
69. Doan L., Bradley K., Gerdes S., and Whalen D.L. J. Org. Chem. 64 (1999) 6227-6234
70. Amyes T.L., Stevens L.W., and Richard J.P. J. Org. Chem. 58 (1993) 6057-6066
71. Sampson K., Paik A., Duvall B., and Whalen D.L. J. Org. Chem. 69 (2004) 5204-5211
72. Balsamo A., Berti G., Crotti P., Ferretti M., Macchia B., and Macchia F. J. Org. Chem. 39 (1974) 2596-2598
73. Whalen D.L., and Ross A.M. J. Am. Chem. Soc. 98 (1976) 7859-7861
74. Richard J.P., Amyes T.L., and Toteva M.M. Acc. Chem. Res. 34 (2001) 981-988
75. Whalen D., Doan L., Poulose B., Friedman S., Gold A., Sangaiah R., Ramesha A., Sayer J., and Jerina D.M. Polycycl. Aromat. Hydrocarb. 21 (2000) 43-52
76. Becker A.R., Janusy J.M., and Bruice T.C. J. Am. Chem. Soc. 102 (1979) 5679-5687
77. Gillilan R.E., Pohl T.M., and Whalen D.L. J. Am. Chem. Soc. 104 (1982) 4481-4482
78. Goering H.L., and Josephson R.R. J. Am. Chem. Soc. 84 (1962) 2779-2785
79. Sayer J.M., Yagi H., Silverton J.V., Friedman S.L., Whalen D.L., and Jerina D.M. J. Am. Chem. Soc. 104 (1982) 1972-1978
80. Doan, L. and Whalen, D.L., unpublished results; (b) Chini, M., Crotti, P., Ferretti, M. and Macchia, F. (1988). Tetrahedron, 44, 2001-2004
81. Swain C.G. J. Am. Chem. Soc. 74 (1951) 4108-4110
82. Long F.A., and Paul M.A. Chem. Rev. 57 (1957) 935-1010
83. Pocker Y., and Ronald B.P. J. Am. Chem. Soc. 100 (1978) 3122-3127
84. Fife T.H. Acc. Chem. Res. 5 (1972) 254-272
85. Fife T.H., and Jao L.K. J. Am. Chem. Soc. 90 (1968) 4081-4085
86. Fife T.H., and Brod L.H. J. Am. Chem. Soc. 92 (1970) 1681-1684
87. Anderson E., and Capon B. J. Chem. Soc. B (1969) 1033-1037
88. Anderson E., and Fife T.H. J. Am. Chem. Soc. 91 (1969) 7163-7166
89. Fife T.H. J. Am. Chem. Soc. 89 (1967) 3228-3231
90. Fife T.H., and Hutchins H.E.C. J. Am. Chem. Soc. 98 (1976) 2536-2543
91. Mori A.L., and Schaleger L.L. J. Am. Chem. Soc. 94 (1972) 5039-5043
92. Dunn B.M., and Bruice T.C. J. Am. Chem. Soc. 93 (1971) 5725-5731
93. Vitullo V.P., and Grossman N.R. J. Org. Chem. 38 (1973) 179-180
94. Kresge A.J., and Chiang Y. J. Am. Chem. Soc. 95 (1973) 803-806
95. Whalen D.L., Weimaster J.F., Ross A.M., and Radhe R. J. Am. Chem. Soc. 98 (1976) 7319-7324
96. Bruice P.Y., Bruice T.C., Dansette P., Selander H.G., Yagi H., and Jerina D.M. J. Am. Chem. Soc. 98 (1976) 2965-2973
97. Mohan, R.S. and Whalen, D.L., unpublished results
98. Kasperek G.J., and Bruice T.C. J. Am. Chem. Soc. 94 (1972) 198-202
99. Sayer J.M., Grossman S.J., Adusei-Poku K.S., and Jerina D.M. J. Am. Chem. Soc. 110 (1988) 5068-5074
100. Whalen D.L., Ross A.M., Montemarano J.A., Thakker D.R., Yagi H., and Jerina D.M. J. Am. Chem. Soc. 101 (1979) 5086-5088
101. Lin B., Islam N., Friedman S., Yagi H., Jerina D.M., and Whalen D.L. J. Am. Chem. Soc. 120 (1998) 4327-4333
102. Islam N.B., Gupta S.C., Yagi H., Jerina D.M., and Whalen D.L. J. Am. Chem. Soc. 112 (1990) 6363-6369
103. Gupta S.C., Pohl T.M., Friedman S.L., Whalen D.L., Yagi H., and Jerina D.M. J. Am. Chem. Soc. 104 (1982) 3101-3104
104. Gupta S.C., Islam N., Whalen D.L., Yagi H., and Jerina D.M. J. Org. Chem. 52 (1987) 3812-3815
105. Jerina D.M., Daly J., Witkop B., Zaltaman-Nirenberg P., and Udenfriend S. Arch. Biochem. Biophys. 128 (1968) 176-183
106. Jerina D.M., Daly J.W., Witkop B., Zaltaman-Nirenberg P., and Udenfriend S. Biochemistry 9 (1970) 147-156
107. Jerina D.M., Daly J.W., and Witkop B. J. Am. Chem. Soc. 90 (1968) 6523-6525
108. Jerina D.M., Daly J.W., Witkop B., Zaltaman-Nirenberg P., and Udenfriend S. J. Am. Chem. Soc. 90 (1968) 6525-6527
109. Boyd D.R., Jerina D.M., and Daly J.W. J. Org. Chem. 35 (1970) 3170-3172
110. Kasperek G.J., and Bruice T.C. J. Am. Chem. Soc. 94 (1972) 198-202
111. Boyd D.R., Daly J.W., and Jerina D.M. Biochemistry 11 (1972) 1961-1966
112. Kasperek G.J., and Bruice T.C. J. Chem. Soc. Chem. Comm. (1972) 784-785
113. Kasperek G.J., Bruice T.C., Yagi H., Kaubisch N., and Jerina D.M. J. Am. Chem. Soc. 94 (1972) 7876-7882
114. Bruice P.Y., Kasperek G.J., and Bruice T.C. J. Am. Chem. Soc. 95 (1973) 1673-1674
115. Kasperek G.J., Bruice P.Y., Bruice T.C., Yagi H., and Jerina D.M. J. Am. Chem. Soc. 95 (1973) 6041-6046
116. Vögel E., and Günther H. Angew. Chem. Int. Ed. Engl. 6 (1967) 385-401
117. Whalen D.L., and Ross A.M. J. Am. Chem. Soc. 96 (1974) 3678-3679
118. Gillilan R.E., Pohl T.M., and Whalen D.L. J. Am. Chem. Soc. 104 (1982) 4482-4484
119. Sridharan, S. and Whalen, D. L., unpublished results
120. Coxon J.M., Maclagan R.G.A.R., Rauk A., Thorpe A.J., and Whalen D.L. J. Am. Chem. Soc. 119 (1997) 4712-4718
121. Whalen D.L., Montemarano J.A., Thakker D.R., Yagi H., and Jerina D.M. J. Am. Chem. Soc. 99 (1977) 5522-5524
122. Doan L., Lin B., Yagi H., Jerina D.M., and Whalen D.L. J. Am. Chem. Soc. 123 (2001) 6785-6791
123. Jencks W.P. J. Am. Chem. Soc. 94 (1972) 4731-4732
124. Jencks W.P. Acc. Chem. Res. 13 (1980) 161-169
125. Woodward R.B., and Hoffman R. The Conservation of Orbital Symmetry (1970), Verlag Chemie, GmbH, Academic Press
126. Ukachukwu V.C., Blumenstein J.J., and Whalen D.L. J. Am. Chem. Soc. 108 (1986) 5039-5040
127. Ukachukwu V.C., and Whalen D.L. Tetrahedron Lett. 29 (1988) 293-296
128. Mohan R.S., Gavardinas K., Kyere S., and Whalen D.L. J. Org. Chem. 65 (2000) 1407-1413
129. Mohan R.S., and Whalen D.L. Org. Chem. 58 (1993) 2663-2669
130. Ritchie C.D., and Virtanen P.O.I. J. Am. Chem. Soc. 94 (1972) 4966-4971
131. Ritchie C.D. Acc. Chem. Res. 5 (1972) 348-354
132. Whalen D.L., Ross A.M., Dansette P.M., and Jerina D.M. J. Am. Chem. Soc. 99 (1977) 5672-5676
133. Nashed N.R., Balani S.K., Loncharich R.J., Sayer J.M., Shipley D.Y., Mohan R.S., Whalen D.L., and Jerina D.M. J. Am. Chem. Soc. 113 (1991) 3910-3919
134. Lin B., Doan L., Yagi H., Jerina D.M., and Whalen D.L. Chem. Res. Toxicol. 11 (1994) 630-638
135. Richard J.P., and Jencks W.P. J. Am. Chem. Soc. 104 (1982) 4689-4691
136. For a review and discussion of literature data for reactions of carbocations with azide ion, see: Ta-Shma, R. and Rappoport, Z. (1983). J. Am. Chem. Soc. 105, 6082-6095
137. Yagi H., Hernandez O., and Jerina D.M. J. Am. Chem. Soc. 97 (1975) 6881-6883
138. Whalen D.L., Ross A.M., Yagi H., Karle J.M., and Jerina D.M. J. Am. Chem. Soc. 100 (1978) 5218-5221
139. Doan L., Yagi H., Jerina D.M., and Whalen D.L. J. Am. Chem. Soc. 124 (2002) 14382-14387
140. Doan L., Yagi H., Jerina D.M., and Whalen D.L. J. Org. Chem. 69 (2004) 8012-8017
141. Curtin D.Y. Rec. Chem. Prog. 15 (1954) 111
142. Eliel, E.L. (1962). Stereochemistry of Carbon Compounds, pp. 151-152, McGraw-Hill, New York