Vinylcyclopropane rearrangements

Chemical Society Reviews

Volumn 17, Issue , 1988, Pages 229-267

  Goldschmidt, Z ^a   Crammer, B ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049090126     PISSN: 03060012     EISSN: None     Source Type: Journal    
DOI: 10.1039/CS9881700229     Document Type: Review

References (165)

1. N. P. Neureiter, J. Org. Ghent., 1959, 24, 2044.
2. U.S. Patent No. 2,951,878 (1960).
3. U.S. Patent No. 2,981,756 (1961).
4. N. J. Demjanow and M. Dojarenko, Chent. Ber., 1922, 55B, 2718.
5. S. H. Harper and H. W. B. Reed, J. Sci. Food Agric., 1951, 414. [The mixture of esters obtained was analysed by n.m.r. and it was found that the methyl irans-5-methyl-2-propen-2-yl-hex-3-enoate was formed in 10% yield—B. Crammer (1988)].
6. H. M. Frey, ‘The gas phase pyrolyses of some small ring compounds), in Advances in Physical Organic Chemistry, 1966, Vol. 4, Ed. V. Gold, Academic Press.
7. S. Sarel, J. Jovell, and M. Sarel-Imber, Angew. Chem., Int. Ed. Engl., 1968, 7, 5.
8. M. R. Willcott III, R. L. Cargill, and A. B. Sears, Prog. Phys. Org. Chem., 1972, 9, 25.
9. M. R. Willcott Jr. and V. H. Cargle, J. Am. Chem. Soc., 1967, 89, 723.
10. R. Breslow, Molecular Rearrangements, 1963, 4, 233.
11. H. M. Frey and R. Walsh, Chem. Rev., 1969, 69, 103.
12. W. R. Dolbier Jr., Acc. Chem. Res., 1981, 14, 195.
13. J. J. Gajewski, ‘Hydrocarbon Thermal Isomerizations’, in Organic Chemistry, A Series of Monographs, Ed. H. A. Wasserman, Academic Press, 1981, p. 5.
14. T. Hudlický, T. M. Kutchan, and S. M. Naqvi, Org. React. (N.Y.), 1985, 33, 247.
15. R. J. Ellis and H. M. Frey, J. Chem. Soc., 1964, 3547.
16. H. M. Frey and D. C. Marshall, J. Chem. Soc., 1962, 3981.
17. R. J. Ellis and H. M. Frey, J. Chem. Soc., 1964, 4188.
18. C. S. Elliot and H. M. Frey, J. Chem. Soc., 1965, 345.
19. R. J. Ellis and H. M. Frey, J. Chem. Soc., 1964, 959.
20. G. R. Branton and H. M. Frey, J. Chem. Soc., (A), 1966, 1342.
21. W. R. Dolbier Jr. and S. F. Sellers, J. Am. Chem. Soc., 1982, 104, 2494.
22. J. M. Simpson and H. G. Richey, Jr., Tetrahedron Lett., 1973, 27, 2545.
23. H. M. Frey and J. A. Krantz, J. Chem. Soc., (A), 1969, 1159.
24. B. M. Trost and P. H. Scudder, J. Org. Chem., 1981, 46, 506.
25. D. W. Shull, Diss. Abstr. B., 1976, 37, 775.
26. C. S. Elliot and H. M. Frey, J. Chem. Soc., 1964, 900.
27. J. Ollivier and J. Salaün, Tetrahedron Lett., 1984, 25, 1269.
28. R. J. Ellis and H. M. Frey, Proc. Chem. Soc. 1964, 221.
29. R. J. Ellis and H. M. Frey, J. Chem. Soc., 1964, 5578.
30. Personal communication from H. M. Frey: the 3-methylcyclopentene was incorrectly reported in reference 26a and the correct product should be 4-methylcyclopentene. S. W. Benson and H. E. O’Neal, ‘Kinetic Data on Gas Phase Unimolecular Reactions’, NSRDS-NBS 21, 1970, 239, U.S. Dept, of Commerce, Washington, D.C.
31. W. R. Dolbier Jr. and S. F. Sellers, J. Org. Chem., 1982, 47, 1.
32. H. G. Richey Jr. and D. W. Shull, Tetrahedron Lett., 1976, 575.
33. P. Y. Bahural, A. Menet, F. Pautet, A. Poncet, and G. Descotes, Bull. Soc. Chim. Fr., 1971, 6, 2215.
34. E. Vogel, Angew. Chem., Int. Ed. Engl., 1963, 2, 1.
35. E. N. Marvell and C. Lin, J. Am. Chem. Soc., 1978, 100, 877.
36. A. F. Thomas and B. Willhalm, Tetrahedron Lett., 1964, 49, 3775.
37. L. H. Zalkow, D. R. Brannon, and J. W. Uecke, J. Org. Chem., 1964, 29, 2786.
38. G. Ohloff, Tetrahedron Lett., 1965, 42, 3795.
39. K. W. Egger, D. M. Golden, and S. W. Benson, J. Am. Chem. Soc., 1964, 86, 5420.
40. M. R. Willcott III. and V. H. Cargle, J. Am. Chem. Soc., 1969, 91, 4310.
41. W. E. von Doering and K. Sachdev, J. Am. Chem. Soc., 1974, 96, 1168.
42. W. E. von Doering and K. Sachdev, ibid., J. Am. Chem. Soc., 1975, 97, 5512.
43. G. D. Andrews and J. E. Baldwin, J. Am. Chem. Soc., 1976, 98, 6705.
44. W. R. Dolbier Jr., O. T. Garza, and B. H. Al-Sader, J. Am. Chem. Soc., 1975, 97, 5038.
45. W. E. von Doering and E. K. G. Schmidt, Tetrahedron, 1971, 27, 2005.
46. R. J. Ellis and H. M. Frey, J. Chem. Soc., (A), 1966, 553.
47. D. S. Glass, R. S. Boikess, and S. Weinstein, Tetrahedron Lett., 1966, 999.
48. R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry’, 1970, Verlag Chemie, Weinheim.
49. H. M. R. Hoffmann, Angew. Chem., Int. Ed. Engl., 1969, 8, 556.
50. R. L. Danheiser, C. Martinez-Davila, and J. M. Morin, J. Org. Chem., 1980, 45, 1340.
51. R. L. Danheiser, C. Martinez-Davila, R. J. Auchus, and J. T. Kadonaga, J. Am. Chem. Soc., 1981,103,2443.
52. R. L. Danheiser, J. J. Bronson, and K. Okano, J. Am. Chem. Soc., 1985, 107, 4579.
53. L. Skattebol, Tetrahedron, 1967, 23, 1107.
54. R. Brun, D. S. B. Grace, K. H. Holm, and L. Skatterbel, Acta Chem. Scand., Ser. B, 1986, 40, 21.
55. M. S. Baird and I. Jefferies, Tetrahedron Lett., 1986, 22, 2493.
56. H. G. Richey, in ‘Carbonium Ions’, Vol. 3, Ed. G. A. Olah and P. von R. Schleyer, Wiley-Interscience, New York, 1972, 1201.
57. For a recent review see, J. Salaun, ‘Rearrangements involving the Cyclopropyl Group’ in ‘The Chemistry of the Cyclopropyl Group, Part I’, ed., Z. Rappoport, Wiley, Chichester, 1987, Ch. 13.
58. R. M. Coates, Progress in the Chemistry of Organic Natural Products, 1976, 33, 73.
59. Z. Goldschmidt, B. Crammer, and R. Ikan, J. Chem. Soc., Perkin Trans. I, 1984, 2697.
60. G. Suzukamo, M. Fukao, and M. Tamura, Tetrahedron Lett., 1984, 25, 1595.
61. D. A. Otieno, G. Pattenden, and C. R. Popplestone, J. Chem. Soc., Perkin Trans. 1, 1977, 196.
62. L. Crombie, P. A. Firth, R. P. Houghton, D. A. Whiting, and D. K. Woods, J. Chem. Soc., Perkin Trans. I, 1972, 642.
63. N. F. Elmore, J. E. Roberts, and G. A. Whitham, J. Chem. Res. (S), 1985, 98.
64. C. D. Poulter, J. Am. Chem. Soc., 1972, 94, 5515.
65. C. D. Poulter, L. L. Marsh, J. M. Hughes, J. C. Argyle, D. M. Satterwhite, R. J. Goodfellow, and S. G. Moesinger, J. Am. Chem. Soc., 1977, 99, 3816.
66. C. D. Poulter and J. M. Hughes, J. Am. Chem. Soc., 1977, 99, 3830.
67. Y. Sakito and G. Suzukamo, Chem. Lett., 1986, 621.
68. E. J. Corey and A. G. Myers, J. Am. Chem. Soc., 1985, 107, 5574.
69. Y. Morizawa, T. Hiyama, and H. Nozaki, Tetrahedron Lett., 1981, 22, 2297.
70. K. B. Wiberg, B. A. Hess, and A. J. Ashe, ‘Carbonium Ions’, Vol. 3, Ed. G. A. Olah and P. von R. Schleyer, Wiley-Interscience, New York, 1972, p. 1295.
71. H. H. Wasserman, R. E. Cochoy, and M. S. Baird, J. Am. Chem. Soc., 1969, 91, 2375.
72. J. P. Barnier and A. J. Salaün, Tetrahedron Lett., 1984, 25, 1273.
73. B. M. Trost and L. N. Jungheim, J. Am. Chem. Soc., 1980, 102, 7910.
74. B. M. Trost and M. K. Mao, J. Am. Chem. Soc., 1983, 105, 6753.
75. D. R. Kelsey and R. G. Bergman, J. Am. Chem. Soc., 1971, 93, 1941.
76. M. Santelli and M. Bertrand, Tetrahedron, 1974, 30, 243.
77. C. H. Heathcock and S. R. Poulter, J. Am. Chem. Soc., 1968, 90, 3766.
78. S. S. Hixon, Org. Photochem., 1979, 4, 218
79. T. Hudlický, T. H. Kutchan, and S. M. Naqvi, Org. React., 1985, 33, 247.
80. E. Lopez and R. D. Doepker, J. Phys. Chem., 1979, 83, 573.
81. W. E. Farneth, M. W. Thomsen, N. L. Schultz, and M. A. Davies, J. Am. Chem. Soc., 1981,103,4001.
82. W. E. Farneth, M. W. Thomsen, and M. A. Berg, J. Am. Chem. Soc., 1979, 101, 6468.
83. R. S. Cooke, J. Chem. Soc., Chem. Commun., 1970, 454.
84. W. J. Leigh and R. Srinivasan, J. Am. Chem. Soc., 1983, 105, 514.
85. R. B. Woodward and R. Hoffmann, ‘The Conservation of Orbital Symmetry’, Verlag Chemie, Weinheim, 1970.
86. M. J. Jorgenson, J. Am. Chem. Soc., 1969, 91, 6432.
87. P. H. Mazzocchi and R. C. Ladenson, J. Chem. Soc., Chem. Comm., 1970, 469.
88. H. Prinzbach, H. Hagemann, J. H. Hartenstein, and R. Kitzing, Chem. Ber., 1965, 98, 2201.
89. W. H. Pirkle and G. F. Koser, Tetrahedron Lett., 1968,129.
90. W. H. Pirkle, S. G. Smith, and G. F. Koser, J. Am. Chem. Soc., 1969, 91, 1580.
91. H. E. Zimmerman and G. E. Samuelson, J. Am. Chem. Soc., 1969, 91, 5307.
92. D. L. Garin and K. O. Henderson, Tetrahedron Lett., 1970, 2009.
93. H. E. Zimmerman and G. A. Epling, J. Am. Chem. Soc., 1972, 94, 8749.
94. T. Sasaki, S. Eguchi, and M. Ohno, J. Org. Chem., 1968, 33, 676.
95. T. Sasaki, S. Eguchi, and M. Ohno, J. Org. Chem., 1970, 35, 790.
96. K. Ueda and M. Matsui, Tetrahedron, 1971, 27, 2771.
97. M. J. Bullivant and G. Pattenden, Pyrethrum Post, 1971, 11, 72.
98. L. O. Ruzo and J. E. Casida, J. Chem. Soc., Perkin Trans. 1, 1980, 728.
99. H. Kristinsson and G. S. Hammond, J. Am. Chem. Soc., 1968, 89, 5970.
100. H. R. Sonawane, B. S. Hanjundiah, and M. U. Kumar, Tetrahedron Lett., 1984, 25, 2245.
101. H. R. Sonawane, B. S. Hanjundiah, and M. U. Kumar, Tetrahedron Lett., 1985, 26, 1097.
102. P. J. Kropp, J. Am. Chem. Soc., 1964, 86, 4053.
103. P. J. Kropp, Org. Photochem., 1967, 1, 1.
104. H. Durr and P. Heitkamper, Liebigs Ann. Chem., 1968, 716, 212.
105. H. Hart and D. C. Lankin, J. Org. Chem., 1968, 33, 4398.
106. H. Perst, Tetrahedron Lett., 1970, 3601.
107. H. E. Zimmerman, Chimia, 1982, 36, 423.
108. H. E. Zimmerman, D. F. Juers, J. H. McCall, and B. Schroder, J. Am. Chem. Soc., 1971, 93, 3662.
109. T. Tabata and H. Hart, Tetrahedron Lett., 1969, 4429.
110. M. Regitz, Angew. Chem., Int. Ed. Engl., 1975, 14, 222.
111. W. T. Borden, J. G. Lee, and S. D. Young, J. Am. Chem. Soc., 1980, 102, 4843.
112. M. G. Barlow, R. H. Hazeldine, and R. Hubbard, J. Chem. Soc., C, 1970, 1232.
113. K. E. Wilzbach and L. Kaplan, J. Am. Chem. Soc., 1965, 87, 4004.
114. L. A. Paquette, G. V. Meehan, R. P. Henzel, and R. F. Eizember, J. Org. Chem., 1973, 38, 3250.
115. S. Sarel, Acc. Chem. Res., 1978, 11, 204.
116. H. Alper, Isr. J. Chem., 1981, 21, 203.
117. K. C. Bishop III, Chem. Rev., 1976, 76, 461.
118. P. A. Pinke, R. D. Stauffer, and R. G. Miller, J. Am. Chem. Soc., 1974, 96, 422.
119. R. G. Salomon, H. F. Salomon, and J. L. C. Kachinski, J. Am. Chem. Soc., 1977, 99, 1043.
120. M. R. Doyle and D. van Leusen, J. Org. Chem., 1982, 47, 5326.
121. L. A. Paquette and M. R. Detty, Tetrahedron Lett., 1978, 713.
122. M. Murukami and S. Nishida, Chem. Lett., 1979, 927.
123. W. E. von Doering and W. R. Roth, Tetrahedron, 1963, 19, 715.
124. R. Grigg, R. Hayes, and A. Sweeney, J. Chem. Soc., Chem. Commun., 1971, 1248.
125. T. Hudlicky, T. M. Kutchan, F. J. Koszyk, and J. P. Sheth, J. Org. Chem., 1980, 45, 5020.
126. Y. Morizawa, K. Oshima, and H. Nozaki, Isr. J. Chem., 1984, 24, 149.
127. J. C. Barborak, L. W. Dasher, A. T. McPhail, J. B. Nichols, and K. D. Onan, Inorg. Chem., 1978, 17, 2936.
128. R. Aumann, Chem. Ber., 1976, 109, 168.
129. Z. Goldschmidt, H. E. Gottlieb, and D. Cohen, J. Organomet. Chem., 1985, 294, 219.
130. W. Grimme, Chem. Ber., 1967, 100, 113.
131. A. Salzer, J. Organomet. Chem., 1976, 117, 245.
132. F. J. Liotta Jr. and B. K. Carpenter, J. Am. Chem. Soc., 1985, 107, 6426.
133. V. Aris, J. M. Brown, J. A. Conneely, B. T. Golding, and D. H. Williamson, J. Chem. Soc., Perkin Trans. 2, 1975, 4.
134. W. Grimme and H. G. Koser, J. Am. Chem. Soc., 1981, 103, 5919.
135. P. M. Warner and S.-L. Lu, J. Am. Chem. Soc., 1980, 102, 331.
136. R. Aumann and W. Worman. Chem. Ber., 1979, 112, 1233.
137. P. Eilbracht and LI. Mayser, Chem. Ber., 1980, 113, 2211.
138. A. D. Keteley and J. A. Braaz, J. Organomet. Chem., 1967, 9, P5.
139. T. Shono, T. Yoshimura, Y. Matsumura, and R. Oda, J. Org. Chem., 1968, 33, 1876.
140. E. Vedejs, J. Am. Chem. Soc., 1968, 90, 4751.
141. S. Sarel, R. Ben-Shoshan, and B. Kirson, J. Am. Chem. Soc., 1965, 87, 2417.
142. R. Ben-Shoshan and S. Sarel, J. Chem. Soc., Chem. Commun., 1969, 883.
143. S. Sarel and M. Langbeheim, J. Chem. Soc., Chem. Commun., 1979, 73.
144. R. Aumann, J. Am. Chem. Soc., 1974, 96, 2631.
145. E. J. Reardon Jr. and M. Brookhart, J. Am. Chem. Soc., 1973, 95, 4311.
146. G. Deganello, H. Maltz, and J. Kozarich, J. Organomet. Chem., 1973, 60, 323.
147. H. R. Beer, P. Bigler, W. von Philipsborn, and A. Salzer, Inorg. Chim. Acta, 1981, 53, L49.
148. R. M. Moriarty, C.-L. Yeh, and K. C. Ramey, J. Am. Chem. Soc., 1971, 93, 6709.
149. D. Entholt, A. Rosan, and M. Rosenblum, J. Organomet. Chem., 1973, 56, 315.
150. A. Eisenstadt, Tetrahedron Lett., 1972, 2005.
151. A. H. Wang, I. C. Paul, and R. Aumann, J. Organomet. Chem., 1974, 69, 301.
152. R. Aumann, Chem. Ber., 1975, 108, 1974.
153. N. W. Alcock, J. M. Brown, J. A. Conneely, and D. H. Williamson, J. Chem. Soc., Perkin Trans. 2, 1979, 962.
154. P. E. Eilbracht and P. Dahler, Chem. Ber., 1980, 113, 542.
155. R. M. Moriarty, K. N. Chen, M. R. Churchill, and S. W. Y. Chang, J. Am. Chem. Soc., 1974, 96, 3661.
156. P. E. Eilbracht, Chem. Ber., 1976, 109, 3136.
157. P. E. Eilbracht, U. Mayser, and G. Tiedtke, Chem. Ber., 1980, 113, 1420.
158. C. Dass, D. A. Peake, and M. L. Gross, Org. Mass Spectrom., 1986, 21, 741.
159. J. P. Dinnocenzo and M. Schmittel, J. Am. Chem. Soc., 1987, 109, 1561.
160. J. P. Dinnocenzo and D. A. Conlon, J. Am. Chem. Soc., 1988, 110, 2324.
161. B. M. Trost, Y. Nishimura, K. Yamamoto, and S. S. McElvain, J. Am. Chem. Soc., 1979, 101, 1328.
162. E. Piers and J. Bauville, J. Chem. Soc., Chem. Commun., 1979, 1138.
163. J. Salaün and J. Ollivier, Nouv. J. Chim., 1981, 5, 587.
164. G. Suzukamo and M. Tamura, Sumitomo Chemical Co., U.S. Patent No. 4,547,586 (1985).
165. A. Fleming, G. Sinai-Zingde, M. Natchus, and T. Hudlicky, Tetrahedron Lett., 1987, 28, 167.