Thermal isomerizations of vinylcyclopropanes to cyclopentenes

Journal of Computational Chemistry

Volumn 19, Issue 2, 1998, Pages 222-231

  Baldwin, John E ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

Cyclopropane stereo mutations; Sigmatropic shift; Vinylcyclopropane

Indexed keywords

EID: 0000177907     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-987X(19980130)19:2<222::AID-JCC15>3.0.CO;2-J     Document Type: Article

References (111)

1. N. P. Neureiter, J. Org Chem., 24, 2044-2046 (1959).
2. E. Vogel, Angew. Chem. 72, 4-26 (1960), note 162; E. Vogel, R. Palm, K. H. Ott, unpublished.
3. E. Vogel, Angew. Chem. 72, 4-26 (1960), note 162; E. Vogel, R. Palm, K. H. Ott, unpublished.
4. C. G. Overberger and A. E. Borchert, J. Am. Chem. Soc., 82, 1007-1008, 4896-4899 (1960).
5. N. J. Demjanow and M. Dojarenko [Ber. Dtsch. Chem. Ges., 55, 2718-2727 (1922)] may have formed some cyclopentene inadvertently as they converted 1-(cyclopropyl)ethyl-trimethylammonium hydroxide to vinylcyclopropane, but the experimental details included in their paper provide no basis for an informed judgment on this possibility.
6. M. C. Flowers and H. M. Frey, J. Chem. Soc., 3547-3548 ( (1961).
7. C. A. Wellington, J. Phys. Chem., 66, 1671-1674 (1962).
8. W. von E. Doering and W. R. Roth, Angew. Chem., Int. Ed. Engl., 2, 115-122 (1963).
9. W. von E. Doering and W. R. Roth, Tetrahedron, 19, 715-737 (1963).
10. S. W. Benson, A. N. Bose, and P. Nangia, J. Am. Chem. Soc., 85, 1388-1389 (1963).
11. K. W. Egger, D. M. Golden, and S. W. Benson, J. Am. Chem. Soc., 86, 5420-5424 (1964).
12. For a more recent experimental determination of the resonance energy of the allyl radical, see W. Tsang and J. A. Walker, J. Phys. Chem., 96, 8378 (1992).
13. H. E. O'Neal and S. W. Benson, J. Phys. Chem., 72, 1866-1887 (1968).
14. H. M. Frey, Adv. Phys. Org. Chem., 4, 147 (1966).
15. S. Sarel, J. Yovell, and H. Sarel-Imber, Angew. Chem., Int. Ed. Engl., 7, 577 (1968).
16. C. D. Gutsche and D. Redmore, Carbocyclic Ring Expansion Reactions, Academic Press, New York, 1968, pp. 163-170.
17. H. M. Frey and R. Walsh, Chem. Rev., 69, 103 (1969).
18. M. R. Willcott, R. L. Cargill, and A. B. Sears, Prog. Phys. Org. Chem., 9, 25 (1972).
19. J. J. Gajewski, Hydrocarbon Thermal Isomerizations, Academic Press, New York, 1980, pp. 81-87.
20. T. Hudlicky, T. M. Kutchan, and S. M. Naqvi, Org. React., 33, 247 (1985).
21. Z. Goldschmidt and B. Crammer, Chem. Soc. Rev., 17, 229 (1988).
22. (a) T. Hudlicky and J. W. Reed, In Comprehensive Organic Synthesis, Vol. 5, B. M. Trost, I. Fleming, and L. A. Paquette, Eds., Pergamon Press, Oxford, 1991, pp. 899-970;
23. (b) T. Hudlicky, D. A. Becker, and R. L. Fan, updated by S. Kozhushkov, In Houben-Weyl: Methods of Organic Chemistry, Vol. E17, Carbocyclic Three- and Four-Membered Ring Compounds, A. de Meijere, Ed., Thieme, Stuttgart, 1996, pp. 2538-2565.
24. E. J. Corey and X.-M. Cheng, The Logic of Chemical Synthesis, John Wiley & Sons, New York, 1989, pp. 88-89.
25. B. S. Rabinovitch, E. W. Schlag, and K. B. Wiberg, J. Chem. Phys., 28, 504 (1958).
26. (a) W. L. Carter and R. G. Bergman, J. Am. Chem. Soc., 90, 7344 (1968);
27. (b) R. G. Bergman, J. Am. Chem. Soc., 91, 7405 (1969);
28. (c) R. G. Bergman and W. I. Carter, J. Am. Chem. Soc., 91, 7411 (1969).
29. J. E. Baldwin and C. B. Selden, J. Am. Chem. Soc., 115, 2239 (1993).
30. R. Hoffmann, Tetrahed. Lett., 3819 (1965).
31. (a) R. Hoffmann, Abstracts of Papers, 151st American Chemical Society National Meeting, Pittsburgh, PA, March 1966; Paper 109 K;
32. (b) R. Hoffmann, Trans. NY Acad. Sci., 475-474 (1966);
33. (c) R. Hoffmann, J. Am. Chem., Soc., 90, 1475 (1968).
34. L. Salem, In Reaction Transition States, 21st Annual Meeting of the Société de Chimie Physique, J.-E. Dubois, Ed., Gordon and Breach, New York, 1972, pp. 97-108.
35. Y. Jean, L. Salem, J. S. Wright, J. A. Horsley, C. Moser, and R. M. Stevens, Pure Appl. Chem., 1 (Suppl.), 197 (1971).
36. J. A. Horsley, Y. Jean, C. Moser, L. Salem, R. M. Stevens, and J. S. Wright, J. Am. Chem. Soc., 94, 274 (1972).
37. P. J. Hay, W. J. Hunt, and W. A. Goddard, J. Am. Chem. Soc., 94, 638 (1972).
38. S. N. Ragunathan, T. B. Freedman, L. A. Nafie, D. K. Lewis, D. A. Glenar, and J. E. Baldwin, J. Am. Chem. Soc., 113, 1864 (1991).
39. T. B. Freedman, S. J. Cianciosi, S. N. Ragunathan, J. E. Baldwin, and L. A. Nafie, J. Am. Chem. Soc., 113, 8298 (1991).
40. J. E. Baldwin and S. J. Cianciosi, J. Am. Chem. Soc., 114, 9401 (1992).
41. J. E. Baldwin, S. J. Cianciosi, D. A. Glenar, G. J. Hoffman, I-W. Wu, and D. K. Lewis, J. Am. Chem. Soc., 114, 9408 (1992).
42. Y. Yamaguchi, H. F. Schaefer, and J. E. Baldwin, Chem. Phys. Lett., 185, 143 (1991).
43. J. E. Baldwin, Y. Yamaguchi, and H. F. Schaefer, J. Phys. Chem., 98, 7513 (1994).
44. S. J. Getty, E. R. Davidson, and W. T. Borden, J. Am. Chem. Soc., 114, 2085 (1992).
45. S. J. Getty, D. A. Hrovat, J. D. Xu, S. A. Barker, and W. T. Borden, J. Chem. Soc. Faraday Trans., 90, 1689 (1994).
46. J. E. Baldwin, In The Chemistry of the Cyclopropyl Group, Vol. 2, Z. Rappoport, Ed., John Wiley & Sons, Chichester, UK, 1995, pp. 469-494.
47. C. Doubleday, J. Phys. Chem., 100, 3520 (1996).
48. C. Doubleday, K. Bolton, G. H. Peslherbe, and W. L. Hase, J. Am. Chem. Soc., 118, 9922 (1996).
49. (a) A. H. Zewail, Lecture, 38th Conference on Chemical Research, Robert A. Welch Foundation, Houston, TX, October 24, 1994, Conference Proceedings, Ch. 8, pp. 129-155;
50. (b) S. Pedersen, J. L. Herek, and A. H. Zewail, Science, 266, 1359 (1994);
51. (c) A. H. Zewail, Lecture, 1995 Peter A. Leermakers Symposium, Wesleyan University, May 4, 1995.
52. J. E. Baldwin, T. B. Freedman, Y. Yamaguchi, and H. F. Schaefer, J. Am. Chem. Soc., 118, 10934 (1996).
53. C. Doubleday, K. Bolton, and W. L. Hase, J. Am. Chem. Soc., 119, 5251 (1997).
54. D. A. Hrovat, S. Fang, W. T. Borden, and B. K. Carpenter, J. Am. Chem. Soc., 119, 5253 (1997).
55. R. B. Woodward and R. Hoffmann, Angew. Chem. Int. Ed. Engl., 8, 781 (1969).
56. R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970, pp. 121-122.
57. M. R. Willcott and V. H. Cargle, J. Am. Chem. Soc., 89, 723 (1967).
58. M. R. Willcott and V. H. Cargle, J. Am. Chem. Soc., 91, 4310 (1969).
59. W. von E. Doering and J. B. Lambert, Tetrahedron, 19, 1989 (1963).
60. W. von E. Doering and E. K. G. Schmidt, Tetrahedron, 27, 2005 (1971).
61. R. A. Clark, Tetrahed. Lett., 2279 (1971).
62. J. S. Swenton and A. Wexler, J. Am. Chem. Soc., 93, 3066 (1971).
63. R. S. Cooke and U. H. Andrews, J. Am. Chem. Soc., 96, 2974 (1974).
64. P. H. Mazzocchi and H. J. Tamburin, J. Am. Chem. Soc., 92, 7220 (1970).
65. P. H. Mazzocchi and H. J. Tamburin, J. Am. Chem. Soc., 97, 555 (1975).
66. W. von E. Doering and K. Sachdev, J. Am. Chem. Soc., 96, 1168 (1974).
67. W. von E. Doering and K. Sachdev, J. Am. Chem. Soc., 97, 5512 (1975).
68. G. D. Andrews and J. E. Baldwin, J. Am. Chem. Soc., 98, 6705 (1976).
69. E. A. Barsa, The Thermal Rearrangements of Substituted Cyclopropanes and the Stereochemistry of the Vinylcyclopropane Rearrangement, Ph.D. Dissertation, Harvard University, 1977.
70. J. J. Gajewski and J. M. Warner, J. Am. Chem. Soc., 106, 802 (1984).
71. R. H. Newman-Evans, R. J. Simon, and B. K. Carpenter, J. Org. Chem., 55, 695 (1990).
72. J. E. Baldwin and N. D. Ghatlia, J. Am. Chem. Soc., 113, 6273 (1991).
73. J. E. Baldwin and S. J. Bonacorsi, J. Am. Chem. Soc., 115, 10621 (1993).
74. J. E. Baldwin and S. J. Bonacorsi, J. Am. Chem. Soc., 59, 7401 (1994).
75. J. E. Baldwin, K. A. Villarica, D. I. Freedberg, and F. A. L. Anet, J. Am. Chem. Soc., 116, 10845 (1994).
76. J. E. Baldwin and K. A. Villarica, J. Org. Chem., 60, 186 (1995).
77. L. A. Asuncion and J. E. Baldwin, J. Org. Chem., 60, 5778 (1995).
78. L. A. Asuncion and J. E. Baldwin, J. Am. Chem. Soc., 117, 10672 (1995).
79. J. E. Baldwin and S. J. Bonacorsi, J. Am. Chem. Soc., 118, 8258 (1996).
80. J. J. Gajewski and M. P. Squicciarini, J. Am. Chem. Soc., 111, 6717 (1989).
81. J. J. Gajewski and L. P. Olson, J. Am. Chem., Soc., 113, 7432 (1991).
82. J. J. Gajewski, L. P. Olson, and M. R. Willcott, J. Am. Chem. Soc., 118, 299 (1996).
83. D. G. Retzloff, B. M. Coull, and J. Coull, J. Phys. Chem., 74, 2455 (1970).
84. D. K. Lewis, J. E. Baldwin, and S. J. Cianciosi, J. Phys. Chem., 94, 7464 (1990).
85. D. K. Lewis, D. J. Charney, B. L. Kalra, A.-M. Plate, M. H. Woodard, S. J. Cianciosi, and J. E. Baldwin, J. Phys. Chem. A, 101, 4097 (1997).
86. For references to the original kinetic work providing data for Figure 1, and for further discussion of the radical stabilization values used, see ref. 40 and J. E. Baldwin, J. Chem. Soc. Chem. Commun., 31 (1988).
87. J. S. Chickos, Abstracts of Papers, 187th American Chemical Society National Meeting, St. Louis, MO, April, 1984, ORGN 228. See also R. J. Crawford and D. M. Cameron, Can. J. Chem., 45, 691 (1967).
88. J. S. Chickos, Abstracts of Papers, 187th American Chemical Society National Meeting, St. Louis, MO, April, 1984, ORGN 228. See also R. J. Crawford and D. M. Cameron, Can. J. Chem., 45, 691 (1967).
89. J. E. Baldwin and K. A. Villarica, Tetrahed. Lett., 35, 7905 (1994).
90. A. de Meijere and W. Lüttke, Tetrahedron, 25, 2047 (1969).
91. M. Traetteberg, P. Bakken, A. Almenningen, and W. Lüttke, J. Mol. Str., 189, 357 (1988).
92. Microwave spectroscopic studies of vinylcyclopropane have provided structural information for the trans conformer: Z. Kisiel, P. W. Fowler, A. C. Legon, and P. Dixneuf, J. Chem. Soc., Faraday Trans., 92, 907 (1996).
93. G. R. De Maré and M. R. Peterson, J. Mol. Struct. (Theochem), 6, 213 (1982).
94. B. Klahn and V. Dyczmons, J. Mol. Struct. (Theochem), 23, 75 (1985).
95. B. K. Carpenter, Acc. Chem. Res., 25, 520 (1992).
96. B. K. Carpenter, J. Org. Chem., 57, 4645 (1992).
97. J. E. Baldwin and K. Belfield, J. Am. Chem. Soc., 110, 296 (1988).
98. F.-G. Klärner, R. Drewes, and D. Hasselmann, J. Am. Chem. Soc., 110, 297 (1988).
99. J. E. Baldwin and K. D. Belfield, J. Phys. Org. Chem., 2, 455 (1989).
100. B. K. Carpenter, J. Am. Chem. Soc., 118, 10329 (1996).
101. M. J. S. Dewar, G. J. Fonken, S. Kirschner, and D. E. Mitner, J. Am. Chem. Soc., 97, 6750 (1975).
102. G. D. Andrews and J. E. Baldwin, J. Am. Chem. Soc., 98, 6706 (1976).
103. J. J. Quirante, R. Enríquez, and J. M. Hernando, J. Mol. Struct. (Theochem), 204, 193 (1990).
104. J. J. Quirante, R. Enríquez, and J. M. Hernando, J. Mol. Struct. (Theochem), 254, 493 (1992).
105. K. N. Houk, Y. Li, and J. D. Evanseck, Angew. Chem. Int. Ed. Engl., 31, 682 (1992); see also K. N. Houk, Acc. Chem. Res., 28, 81 (1995).
106. K. N. Houk, Y. Li, and J. D. Evanseck, Angew. Chem. Int. Ed. Engl., 31, 682 (1992); see also K. N. Houk, Acc. Chem. Res., 28, 81 (1995).
107. O. Wiest, J. Storer, J. Fennen, M. Nendel, and K. N. Houk, Abstracts of Papers, 210th American Chemical Society National Meeting, Chicago, IL, August 1995, ORGN 33.
108. K. N. Houk, M. Nendel, O. Wiest, and J. W. Storer, J. Am. Chem. Soc., 119, 10545 (1997).
109. E. R. Davidson and J. J. Gajewski, J. Am. Chem. Soc., 119, 10543 (1997).
110. (a) D. K. Lewis, B. Brandt, L. Crockford, D. A. Glenar, G. Rauscher, J. Rodrequez, and J. E. Baldwin, J. Am. Chem. Soc., 115, 10621 (1993);
111. (b) D. K. Lewis, A. Hutchinson, S. J. Lever, E. L. Spaulding, S. J. Bonacorsi, and J. E. Baldwin, Israel J. Chem., 36, 233 (1966).