Transition metal-stabilized carbocations in organic synthesis

The Chemistry of the Metal-Carbon Bond

Volumn 4, Issue , 2010, Pages 889-978

  Pearson, Anthony J ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

Michael addition; Organometallic; Reaction equivalents; Robinson annulation; Synthons

Indexed keywords

ADDITION REACTIONS; ORGANOMETALLICS;

CARBOCATIONS; MICHAEL ADDITIONS; ORGANIC SYNTHESIS; REACTION EQUIVALENTS; ROBINSON ANNULATION; SYNTHONS;

TRANSITION METALS;

EID: 84949479480     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470771778.ch10     Document Type: Chapter

References (281)

1. S. G. Davies, M. L. H. Green, and D. M. P. Mingos, Tetrahedron, 175, 113 (1978).
2. A. Jungbaur and H. Behrens, Z. Naturforsch., Teil B. 33, 1083 (1978);
3. E. O. Fischer and A.Vogler, Z. Nalurforsch.. Teil B, 17, 421 (1962);
4. J. W. Faller, and B. V. Johnson, J . Organomel.Chem., 88, 101 (1975).
5. M. Rosenblum, Acc. Chem. Res., 7, 122 (1974).
6. P. F. Boyle and K. M. Nicholas, J. Org. Chem., 40, 2682 (1975).
7. P. Lemon, M. Madhavarao, A. Rosan, and M. Rosenblum, J. Organomet. Chem., 108,93 (1976);
8. A. Rosan, M. Rosenblum, and J. Tancrede,J. Am. Chem. Soc.,95,3062(1973).
9. P . Lennon,A. M.Rosan, and M. Rosenblum, J . Am. Chem. Soc.,99,8426(1977)
10. K. M. Nicholas, A. M. Rosan, and M. Rosenblum, J . Organomel. Chem., 84, 351 (1975).
11. T. C. T. Chang and M. Rosenblum, J. Org. Chem., 46, 4103 (1981).
12. T. C. T. Chang and M. Rosenblum, J.Org. Chem. 46, 4627 (1981).
13. S. R. Berryhill and M. Rosenblum, J .Org.Chem., 45, 1984 (1980).
14. D. F. Martin, J. Chem. Soc., Chem. Commun., 341 (1980).
15. D. J. Bates, M. Rosenblum, and S. B. Samuels, J. Organomet. Chem., 209, C55 (1981).
16. D. L. Reger and P. J. McElligott, J . Am. Chem. Soc., 102, 5923 (1980).
17. A. M. Rosan and M. Rosenblum. J. Org. Chem., 40, 3621 (1975).
18. N. Genco, D. Marten, S. Raghu, and M. Rosenblum, J . Am. Chem. Soc., 98, 848 (1976).
19. K. M. Nicholas, J . Am. Chem. Soc., 97, 3254 (1975).
20. G .W. Parshall, Homogeneous Catalysis, Wiley, New York, 1980, Chapter 6.
21. J. Tsuji, Organic Synthesis with Palladium Compounds, Springer-Verlag. Berlin, 1980, Chapter 3.
22. J . Tsuji, M. Kaito, and T. Takahashi, Bull. Chem. Soc. Jpn., 51, 547 (1978).
23. C. S. Subraminiam, P. J. Thomas, V. R. Marndapur, and M. S. Chadha, Synthesis, 468 (1978).
24. J. Tsuji, M. Kaito, T. Yamada, and T. Mandai, Bull. Chem. Soc. Jpn., 51, 1915 (1978).
25. J. Tsuji and T. Mandai, Tetrahedron Lett., 1817 (1978).
26. T. Yanami. M. Miyashita, and A. Yoshikoshi, J. Org. Chem., 45. 607 (1980).
27. J. Tsuji, I. Shimizu, H. Suzuki, and Y. Naito, J . Am. Chem. Soc., 101, 5070 (1979).
28. M. Shibasaki, K. Iseki, and S . Ikegami, Tetrahedron Lett., 21, 3587 (1980).
29. P. D. Magnus and M. S . Nobbs, Synth. Commun., 10,273 (1980);
30. H. Yatagai, Y. Yamamoto, andK. Maruyama, J . Am. Chem. Soc., 102, 4548 (1980);
31. A. J. G. Baxter, K. H. Dickinson, P. M.Roberts, T. C. Smale. and R. Southgate, J. Chem. Soc. Chem. Commun., 236(1979);
32. W. G .Lloydand B. J. Luberoff, J . Org. Chem., 34, 3949 (1969);
33. J. Tsuji, Y. Kobayashi, and T. Takahashi,Tetrahedron Lett., 21, 483 (1980).
34. J. Tsuji, M. Takahashi, and T. Takahashi, Tetrahedron Lett., 21, 849 (1980).
35. I. I. Moiseev, M. N. Vargaftik, and Y. K. Syrkin, Dokl. Akad. Nauk. SSSR, 133, 377 (1960).
36. W. Kitching, Z. Rappoport, S. Winstein, and W. C. Young, J . Am. Chem. Soc., 88,2054 (1966).
37. N. Adachi, K. Kikukawa, M. Takagi,and T. Matsuda, Bull. Chem. Soc. Jpn.,48,521(1975);
38. C.B.Anderson and B. J. Burreson, Chem. Ind . (London), 620 (1967)
39. D. E. James and J. K. Stille, J . Am. Chem. Soc., 98, 1810 (1976);
40. J. K. Stille and D. E. James, J.Am. Chem. Soc.,97,674(1975);
41. J. K. Stille and D. E. James,J. Organomet. Chem., 108,401 (1976);
42. J. K. Stille and R. Bivakaruni, J. Am. Chem. Soc., 100, 1303 (1978).
43. M. F. Semmelhack and C. Bodurow, J .Am. Chem. Soc., 106, 1496 (1984).
44. J. E. Backvall, Tetrahedron Lett., 467 (1977).
45. L. S. Hegedus, G. F. Allen, and E. L. Waterman, J. Am. Chem. Soc., 98, 2674 (1976);
46. L. S. Hegedus, G. F. Allen, J. J. Bozell, and E. L. Waterman, J. Am. Chem. Soc., 100, 5800 (1978).
47. A. Kasahara and N. Fukuda, Chem. Ind. (London), 485 (1976).
48. D. E. Korte, L. S. Hegedus. and R. K. Wirth, J . Org. Chem., 42, 1329 (1977).
49. S. I. Murahashi and T. Yano, J. Am.Chem. Soc., 102, 2456 (1980).
50. Y. Odaira, T. Oishi, T. Yukawa, and S. Tsutsumi, J. Am. Chem. Soc., 88,4105 (1966);
51. E. S. Brownand E. A. Rick, Chem. Commun., 112 (1969);
52. E. S. Brown, E. A. Rick, and F. D. Mendicino, J .Organomet. Chem., 38, 37 (1972).
53. B. M. Trost and T. R. Verhoeven, in Comprehensiue Orgonometallic Chemistry (Eds. G. Wilkinson, F. G. A. Stone, and E. W. Abel), Vol. 8, Pergamon Press, Oxford, 1982, p. 881.
54. R. F. Heck, Acc. Chem. Res., 12, 146 (1979).
55. Y. Fujiwara, I. Moritani, S. Danno, R. Asano, and S. Teranishi, J . Am. Chem. Soc., 91, 7166(1969);
56. Y. Fujiwara, I. Moritani, R. Asano, H. Tanaka, and S. Teranishi, Tetrahedron, 25,4815(1969);
57. Y. Fujiwara, R. Asano, I. Moritani, and S . Teranishi, J. Org. Chem., 41, 1681 (1976).
58. B. M. Trost, S. A. Godleski, and J. P. Genet, J. Am. Chem. Soc., 100, 3930 (1978);
59. B. M. Trost S. A. Godleski, and J. Belletire, J . Org. Chem., 44, 2052 (1979).
60. H. Takahashi and J. Tsuji, J. Am. Chem. Soc., 90, 2387 (1968).
61. R. A. Holton, J . Am. Chem. Soc., 99, 8083 (1977).
62. L. S. Hegedus, T. Hayashi and W. H. Darlington, J. Am. Chem. Soc., 100, 7747 (1978).
63. T. Hayashi and L. S. Hegedus, J. Am. Chem. Soc., 99, 7093 (1977).
64. L. S. Hegedus, R. E. Williams, M. A. McGuire, and T. Hayashi, J . Am. Chem. Soc., 102, 4973(1980).
65. R. Huttel and M. McNiff, Chem. Ber., 106, 1789 (1973);
66. B. M. Trost, P. E. Strege, L. Weber, T. J.Fullerton, and T. J. Dietsche, J. Am. Chem. Soc., 100,3407 (1978);
67. P. S. Manchand, H. S. Wong, and J. F. Blount, J . Org. Chem., 43,4769 (1978);
68. K. Henderson and F. J. McQuillin, J. Chem. Soc. Chem. Commun., 15 (1978);
69. P. Boontanonda and R. Grilff, J . Chem. Soc.. Chem. Commun., 583 (1977).
70. B. M. Trost and L. Weber, J. Org. Chem., 40, 3617 (1975).
71. B . M. Trost and P. J. Metzner, J. Am. Chem. Soc. 102, 3572 (1980).
72. D. J. Collins. W. R. Jackson, and R. N. Timms, Aust. J . Chem., 30, 2167 (1973).
73. J. Y. Sato and C. A. Horiuchi, Bull. Chem. Soc. Jpn., 52,2653 (1979).
74. E. Samuel and M. Bigorgne, J. Organomet. Chem., 19, 9 (1969).
75. J. M. Kliegman, J. Organomet. Chem., 29, 73 (1971);
76. K. Yamamoto, K. Shinohara, T. Ohuchi, and M. Kumada, Tetrahedron Lett., 1153 (1974);
77. S. Lin and P. Boudjouk, J . Organomet. Chem., 187, C11 (1980);
78. K. Itoh, M. Fukui. and Y. Kurachi, J. Chem. Soc., Chem. Commun., 500 (1977).
79. E. O. Fischer and G. Burger, Z. Naturforsch., 616, 702 (1961):
80. W. T. Dent, R. Long, and G. Wilkinson, J. Chem. Soc., 1585 (1964).
81. P. M. Maitlis, The Organic Chemistry of Palladium, Vols. 1 and 2, Academic Press, New York, 1971;
82. see also ref. 16 and 37.
83. P. E. Slade, Jr., and H. B. Jonassen, J . Am. Chem. Soc., 72, 1277 (1957);
84. E. O. Fischer and H. Werner, Chem. Ber., 93,2075 (1962);
85. S .D. Robinson and B. L. Shaw, J. Chem. Soc., 4806 (1963);
86. S .D. Robinson and B. L. Shaw, J. Chem. Soc.,5002 (1964);
87. B. L. Shaw, Chem. Ind. (London), 1190 (1962);
88. R. P. Hughes, D. E. Hunton and K. Schumann, J . Organomet. Chem., 169, C37 (1969);
89. R. Noyori and H. Takaya, Chem. Commun., 525 (1969).
90. B. M. Trost and P. E. Strege, J . Am. Chem. Soc., 97, 2534 (1975);
91. B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, and T. J. Dietsche, J. Am. Chem. Soc., 100, 3416 (1978).
92. D. J. Collins, W. R. Jackson, and R. N. Timms, Tetrahedron Lett., 495 (1976).
93. B. M. Trost and T. R. Verhoeven, J .Am.Chem. Soc., 98, 630 (1976);
94. B. M. Trost and T. R. Verhoeven, J .Am. Chem. Soc.,100, 3435 (1978).
95. W. R. Jackson and J. V. Strauss, Tetrahedron Lett., 2591 (1975);
96. W. R. Jackson and J. V. StraussAust. J . Chem., 30,553 (1977).
97. See B. M. Trost et al.,ref. 46 and 47.
98. J. S. Temple and J. Schwartz, J. Am. Chem. Soc., 102, 7381 (1980).
99. R. A. Clement, V. Klabunde, and G. W. Parshall, J. Mol. Catal., 4, 87 (1978).
100. D. N. Jones and S. D. Knox, J . Chem. Soc.. Chem. Commun., 165 (1975).
101. F. G. Stankem and R. F. Heck, J . Org. Chem., 45,3584 (1980);
102. B. Akermark and K. Zetterberg,Tetrahedron Lett., 3733 (1975);
103. B. Akerrnark, J. E. Backvall, A. Lowenborg, and K. Zetterberg, J.Organomet. Chem., 166, C33 (1979).
104. I. T. Harrison, E. Kirnura, E. Bohme. and J. H. Fried, Tetrahedron Letf., 1589 (1969);
105. W. R.Jackson and J. V. Strauss, Aust. J . Chem., 31, 1073 (1978).
106. B. M. Trost and T. R. Verhoeven, J. Am. Chem. Soc., 102.4730 (1980).
107. See ref. 37, p. 827.
108. B. M. Trost and F. W. Gowland, J. Org. Chem., 44, 3448 (1979).
109. B. M. Trost and D. P. Curran, J. Am. Chem. Soc., 102, 5699 (1980).
110. B. M. Trost, T. R. Verhoeven, and J. M. Fortunak, Tetrahedron Lett., 2301 (1979).
111. B. M. Trost and T. P. Klun, J. Am. Chem. Soc., 103, 1864 (1981).
112. B. M. Trost and T. R. Verhoeven, J . Org. Chem., 41, 3215 (1976).
113. See ref. 37, p. 826.
114. B. M. Trost and E. Keinan, Tetrahedron Lett., 2591 (1980).
115. B. M. Trost and E. Keinan, Tetrahedron Lett., 2595 (1980).
116. B. M. Trost and J. P. Genet, J . Am. Chem. Soc., 98,8516 (1976);
117. G. Hata, K. Takahashi and A.Miyake, Chem. Commun., 1392 (1970);
118. K. E. Atkins, W. E. Walker, and R. M. Manyik,Tetrahedron Lett., 3821 (1970);
119. K. Takahashi, A. Miyake, and G. Hata, Bull. Chem. Soc jpn., 45,230 (1972);
120. S. I. Murahashi, T. Shimamura and I. Moritani, J. Chem. Soc. Chem. Commun., 931(1974);
121. H. H. Baer and Z. S . Hanna, Carbohydr. Res., 78, C11 (1980).
122. B. M. Trost and E. Keinan, J. Org. Chem., 44, 3451 (1979);
123. B. M. Trost and E. Keinan, J. Org. Chem.,45, 2741 (1980).
124. W. Carruthers and S. A. Cumming, J . Chem. Soc., Chem. Commun., 360 (1983);
125. S. A. Godleski, D. J. Heathcock, J. D. Meinhart, and S. Van Wallendael, J .Org. Chem., 48, 2101 (1983).
126. S. W. McCombie, Eur. Pat., EPO-013-663-Al (1980).
127. K. Takahashi, G .Hata, and A. Miyake, Bull. Chem. Soc. Jpn., 46, 1012 (1973);
128. D. G. Brady, Chem. Commun., 434 (1970).
129. P. A. Grieco, T. Takigawa, S. L. Bongers, and H. Tanaka, J. Am. Chem. Soc., 102,7588 (1980).
130. B. M. Trost and T. R. Verhoeven, J. Am. Chem. Soc., 102, 4743 (1980).
131. J. Tsuji, Y. Kobayashi, H. Kataoka, and T. Takahashi, Tetrahedron Lett., 1475 (1980).
132. B. M. Trost and T. R. Verhoeven, J. Am. Chem. Soc., 101, 1595 (1979).
133. J. Tsuji, Y. Kobayashi, H. Kataoka, and T. Takahashi, Tetrahedron Lett., 3393 (1980).
134. V. Kitagawa, A. Itoh, S. Hashimoto, H. Yamamoto, and H. Nozaki, J . Am. Chem. Soc., 99,3864, (1977).
135. B. M. Trost, T. A. Runge, and L. N. Jungheim, J. Am. Chem. Soc., 102, 2840 (1980).
136. See ref. 37, p. 834.
137. B. M. Trost and J. Fortunak, J. Am. Chem. Soc., 102, 2841 (1980).
138. I. Shimizu, T. Yamada, and J. Tsuji, Tetrahedron Lett., 3199 (1980).
139. R. G. Hayter, J. Organomet. Chem., 13, P1 (1963).
140. N. A. Bailey, W. G. Kita, J. A. McCleverty, A. J. Murray, B. E. Mann. and N. W. J. Walker, J. Chem. Soc.. Chem. Commun. 592 (1974).
141. J. W. Faller and A. M. Rosan, J. Am. Chem. Soc., 98, 3388 (1976).
142. R. D. Adams, D. F. Chodosh, J. W. Faller,and A. M. Rosan, J. Am. Chem. Soc., 101,2590(1979).
143. B. E. R. Schilling, R. Hoffman, and J. W. Faller, J. Am. Chem. Sou.. 101, 5921 (1979).
144. B. M. Trost and M. Lautens, J. Am. Chem. Soc., 104, 5543 (1982).
145. B. M. Trost and M. Lautens, J . Am. Chem. Soc., 105, 3343 (1983).
146. S .F. Martin, Tetrahedron, 36, 419 (1980).
147. B. M. Trost and M. H. Hung, J . Am. Chem. Soc., 105, 7757 (1983).
148. R. A. Plowman and F. G . A. Stone, Z. Naturforsch.. Teil B, 17, 575 (1962).
149. H. D. Murdoch and E . Weiss, Helu. Chim. Acta, 45, 1927 (1962).
150. T. H. Whitesides, R. W. Arhart, and R. W. Slaven, J. Am. Chem. Soc., 95, 5792 (1973).
151. G. F. Emerson and R. Pettit, 84, 4591 (1962);
152. D. H. Gibson and R. L.Vonnahme, J. Am. Chem. Soc., 94, 5090 (1972);
153. D. H. Gibson and R. L.Vonnahme,J . Organomet. Chem., 70, C33 (1974)
154. A. J. Pearson, Aust. J . Chem., 29, 1841 (1976).
155. A. J. Pearson, Tetrahedron Lett., 3617 (1975).
156. J. L. Roustan, J. Y. Mérour and F. Houlihan, Tetrahedron Lett., 3721 (1979).
157. R. Palumbo, A. De Renzi, A. Panunji, and G .Paiaro, J.Am. Chem. Soc., 91,3874;
158. R. Palumbo, A. De Renzi, A. Panunji, and G .Paiaro, J.Am. Chem. Soc., 3879 (1969);
159. J.Tsuji and H. Takahashi, J . Am. Chem. Soc., 87,3275 (1965);
160. M. Tada, Y. Kuroda, and T. Sato,Tetrahedron Lett., 2871 (1969).
161. W. C. Still and I. Galynker, Tetrahedron, 37, 3981 (1981);
162. W. C. Still and I. Galynker J . Am. Chem. Soc., 104, 1774 (1982).
163. J. W. Faller and A. M. Rosan, Ann. N . Y . Acad. Sci.,295, 186(1977);
164. J. W. Faller and A. M. Rosan J . Am. Chem. Soc., 99,4858 (1977);
165. M. L. H. Green, J. Knight, and J. A. Segal, J. Chem. Soc., Dalton Trans., 2189 (1977).
166. J. W. Faller, H. H. Murray, D. L. White, and K. H. Chao, Organometallics, 2, 400 (1983).
167. A. J. Pearson and Md. N. I. Khan, J. Am. Chem. Soc., 106, 1872 (1984);
168. A. J. Pearson and Md. N. I. Khan Tetrahedron Lett., 25,3507 (1984).
169. A. J. Pearson, Acc. Chem. Res., 13,463 (1980);
170. A. J. Pearson in Comprehensiue Organometallic Chemistry(Eds. G Wilkinson, F. G. A. Stone, and E. W. Abel), Vol. 8, Pergamon Press, Oxford,1982, Chapter 58;
171. A. J. Pearson Transition Met. Chem., 6,67 (1981);
172. A. J. Pearson Chem. Ind. (London), 741 (1982);
173. A. J. Pearson Science,223, 895 (1984);
174. A. J. Pearson Pure Appl. Chem., 55, 1767 (1983).
175. E. O. Fischer and R. D. Fischer, Angew. Chem., 72, 919 (1960).
176. M. de M. Carnpos and N. Petragnani, Tetrahedron Lett., 6,11 (1959);
177. M. de M. Carnpos and N. Petragnani Chem. Ber., 93,317 (1960);
178. K. C. Nicolaou, S. P. Seitz W. J. Sipio, and J. F. Blount, J.Am. Chem. Soc., 101, 3884 (1979);
179. D. L. J. Clive, V. Farina, A. Singh, C. K. Wong, W. A. Kiel, and S. M. Menchen, J. Org. Chem., 45, 2120 (1980);
180. K. C. Nicolaou, Tetrahedron, 37, 4097 (1981).
181. K. B. Sharpless and R. F. Lauer, J . Am. Chem. Soc., 94,7154(1972);
182. K. B. Sharpless and R. F. Lauer, J . Am. Chem. Soc., 95,2697 (1973);
183. H. J. Reich,J. Org. Chem., 40, 2570 (1975).
184. A. J. Pearson. T. Ray, I. C. Richards, J. Clardy, and L. Silveira, Tetrahedron Lett., 24, 5827(1983);
185. A. J. Pearson and T. Ray, Tetrahedron, 41, 5765 (1985).
186. A. J. Birch and M. A. Haas, J . Chem. Soc. C , 2465 (1971).
187. Y. Shvo and E. Hazum. J.Chem. Soc. Chem. Commun., 336 (1974).
188. S. Warren, Organic Synthesis: The Disconnection Approach, Wiley, Chichester, 1982.
189. A. J. Birch, K. B. Chamberlain, M. A. Haas, and D. J. Thompson, J.Chem.Soc.,Perkin Trans. I ,1882 (1973);
190. A. J. Birch and A. J. Pearson, J. Chem. Soc.. Perkin Trans. I , 954 (1976);
191. R. E.Ireland, G. G. Brown, R. H. Stanford, Jr., and T. C. McKenzie, J. Org. Chem., 39,51 (1974);
192. A. J.Birch, A. S. Narula, P. Dahler, G. R. Stephenson, and L. F. Kelly, Tetrahedron Len., 21, 979(1980);
193. A. J. Birch, A. J. Liepa, and G. R. Stephenson, Tetrahedron Lett., 3565 (1979);
194. G . R. John and L. A. P. Kane-Maguire, J . Chem. Soc.. Dalton Trans., 1196 (1979);
195. L. A. P. Kane-Maguire and C. A. Mansfield, J.Chem. Soc. Chem. Commun., 540 (1973);
196. C. A. Mansfield, K. M. Al-Kathumi, and L. A. P. Kane-Maguire, J.Orgonomet. Chem., 71, C11 (1974);
197. A. J. Birch and A. J. Pearson, Tetrahedron Lett., 2379 (1975);
198. A. J. Pearson, Aust. J. Chem., 30, 345 (1977);
199. A. Pelter. K. J. Could, and L. A. P. Kane-Maguire, J.Chem. Soc. Chem. Commun., 1029 (1974);
200. M. Cower, G .R. John, L. A. P. Kane-Maguire, T. I. Odiaka, and A. Salzer, J.Chem. Soc..Dalton Trans., 2003 (1979);
201. A. J. Birch, I. D. Jenkins, and A. J. Liepa, Tetrahedron Lett., 1723 ( 1975);
202. see also ref. 112.
203. A. J. Pearson and C. W. Ong, J . Am. Chem. Soc., 103. 6686 (1981).
204. O. Eisenstein, W. Butler, and A. J. Pearson, Organometallics, 3, 1150 (1984).
205. Ch. Tamrn, Fortschr. Chem. Org. Naturst., 31, 63 (1974);
206. J. R. Bamburg and F. M. Strong, in Microbial Toxins (Eds. S. Kadis, A. Ciegler, and S. J. Ajl), Vol. 3, Academic Press, New York, 1971, p. 207.
207. A. J. Pearson, E. Mincione, M. Chandler, and P. R. Raithby, J.Chem. Soc.. Perkin Trans. I , 2774 (1980);
208. A. J. Pearson and G. C. Heywood, Tetrahedron Lett., 22, 1645 (1981);
209. E. Mincione, A. J.Pearson, P. Bovicelli, M. Chandler, and G .C. Heywood, Tetrahedron Lett., 22,2929 (1981);
210. A. J.Pearson, G. C. Heywood, and M. Chandler, J.Chem. Soc., Perkin Trans.I , 2631 (1982).
211. G. R. Han, Ph.D. Dissertation, Case Western Reserve University, 1986.
212. W. S. Johnson, J. C. Collins, R. Pappo, and M. B. Rubin, J.Am. Chem. Soc.,80,2585 (1958), and references cited therein;
213. W. S. Johnson, W. A. Vredenburgh, and J. E. Pike, J.Am. Chem. Soc. 82, 3409 (1960).
214. Review: E. Brown and M. Ragault, Tetrahedron, 35, 911 (1979).
215. A. J. Pearson and D. C. Rees, Tetrahedron Lett., 21, 3937 (1980);
216. A. J. Pearson and D. C. ReesJ . Am. Chem. Soc., 104. 1118 (1982);
217. A. J. Pearson and D. C. Rees J . Chem. Soc. Perkin Trans. I , 2467 (1982);
218. A. J. Pearson, Tetrahedron Lett., 22, 4033 (1981);
219. A. J. Pearson, D. C. Rees, and C. W. Thornber, J . Chem. Soc. Perkin Trans. I . 625 (1983).
220. A. J. Birch, W. D. Raverty, and G . R. Stephenson, J.Chem. Soc., Chem. Commun., 857 (1980);
221. A. J. Birch and G . R. Stephenson, Tetrahedron Lett., 22,779 (1981);
222. A. J. Birch, W. D. Raverty, and G. R. Stephenson, Tetrahedron Lett., 21, 197 (1980);
223. A. J. Birch and B. M. R. Bandara, Tetrahedron Lett., 21, 2981 (1980);
224. B. M. R. Bandara, A. J. Birch, L. F. Kelly, and T. C. Khor.Tetrahedron Lett.. 24, 2491 (1983).
225. A. J. Pearson. J . Chem. Soc..Perkin Trans. I, 1255 (1979);
226. A. J. Pearson. J . Chem. Soc..Perkin Trans. I, 400 ( 1980);
227. A. J. Pearson. P. Ham and D. C. Rees, J.Chem. Soc., Perkin Trans. I , 489 (1982);
228. A. J. Pearson, T. R. Perrior and D. A. Griffin, J. Chem. Soc.. Perkin Trans.I ,625 (1983);
229. A. J. Pearson and T. R. Perrior, J. Organomet.Chem., 285, 253 (1985).
230. Review: J. A. Marshall, S. F. Brady, and N. H. Andersen, Fortschr. Chem. Org. Naturst., 31,283, (1974).
231. A. J. Pearson. P. Ham, and D. C. Rees, Tetrahedron Lett., 21,4637 (1980);
232. A. J. Pearson and P.Ham, J. Chem. Soc. Perkin Trans. I , 1421 (1983).
233. A. J . Birch, P. E. Cross, J. Lewis, D. A. White, and S. B . Wild, J.Chem. Soc. A , 332 (1968);
234. L. F.Kelly, A. S. Narula, and A. J. Birch, Tetrahedron Lett.. 21, 2455 (1980);
235. A. J. Birch, L. F. Kelly, and D. J. Thompson, J.Chem. Soc., Perkin Trans.I , 1006 (1981);
236. L. F. Kelly, P. Dahler, A. S. Narula, and A. J. Birch, Tetrahedron Lett., 22, 1433 (1981).
237. A. J. Birch, P. Dahler, A. S. Narula, and G. R. Stephenson, Tetrahedron Lett., 21, 3817 (1980).
238. A. J. Pearson, D. V. Gardner, and I . C. Richards, J.Chem. Soc.. Chem. Commun., 807 (1982);
239. A. J. Pearson, D. V. Gardner, and I . C. Richards, J . Org. Chem., 49, 3887 (1984).
240. I. H. Sanchez and F. R. Tallabs, Chem. Lett., 891 (1981).
241. A. J. Pearson and C. W. Ong, J. Org.Chem., 47, 3780 (1982).
242. A. J. Pearson and C. W. Ong, J. Chem. Soc.. Perkin Trans. I , 1614 (1981);
243. A. J. Pearson and M. Chandler, Tetrahedron Lett., 21, 3933 (1980);
244. A. J. Pearson and M. Chandler J . Chem. Soc.. Perkin Trans I. , 2467 (1982);
245. A.J. Pearson, J.Chem. Soc., Chem. Commun., 488 (1980).
246. L. A. Paquette, R. G . Daniels, and R. Gleiter, Organometallics, 3, 560 (1984).
247. R. Aumann, J.Organomet. Chem., 47, C28(1973);
248. R. Edwards. J. A. S. Howell, B. F. G. Johnson,and J. Lewis, J.Chem. Soc.. Dalton Trans., 2105 (1974);
249. R. Burton, M. L. H. Green, E. W. Abel, and G. Wilkinson, Chem. Ind. (London), 1952 (1958);
250. R. Burton, L. Pratt, and G. Wilkinson, J.Chem. Soc., 594 (1961);
251. H. J. Dauben and D. Bertelli, J.Am. Chem. Soc., 83,497 (1961);
252. M. A.Hashmi, J. D. Munro, P. L. Pauson, and J. M. Williamson, J. Chem. Soc. A, 240 (1967);
253. J. Evans,D. V. Howe, B . F. G. Johnson, and J. Lewis, J . Organornet. Chem., 61, C48 (1973);
254. D. A. Brown,S. K. Chawla, and W. K. Glass, Inorg. Chim. Acto, 19, L31 (1976);
255. L. A. P. Kane-Maguire, T. I.Odiaka, and P. A. Williams, J.Chem. Soc., Dalton Trans., 200 (1981);
256. P. Hackett, B. F. G.Johnson, J. Lewis, and G. Jaouen, J . Chem. Soc.. Dalton Trans., 1247 (1982).
257. A. J. Pearson, S. L. Kole, and B. Chen, J. Am. Chem. Soc., 105, 4483 (1983).
258. A. J. Pearson, S.L. Kole, and T. Ray, J.Am. Chem. Soc., 106, 6060(1984).
259. Review: K. M. Nicholas, M. O. Nestle, and D. Seyferth, in Transition Metal Organomerallics in Organic Synthesis (Ed. H. Alper), Vol.2, Academic Press, New York. 1978, Chapter 1 .
260. K. M. Nicholas, M. Mulvaney and M. Bayer, J. Am. Chem. Soc., 102,2508 (1980);
261. J. O'Boyle and K. M. Nicholas, Tetrahedron Lett., 21, 1595 (1980);
262. R . Lockwood and K. M. Nicholas, Tetrahedron Lett., 4163 (1977).
263. G . Jaouen, in Transition Meral Organometallics in Organic Synthesis (Ed. H. Alper), Vol. 2, Academic Press, New York, 1978, Chapter 2;
264. M. F. Semmelhack, Tetrahedron, 37,3956 (1981);
265. M. F. Semmelhack Ann. N . Y. Acad. Sci., 295, 36 (1977);
266. G . Jaouen. Ann. N. Y. Acad. Sci.. 295, 59 (1977).
267. T. H. Collield, V. Sandel, and R. D. Closson, J. Am. Chem. Soc., 79,5826(1957);
268. G .Winkhaus, L. Pratt, and G .Wilkinson. J. Chem. Soc., 3807 (1961);
269. P. L. Pauson and J. A. Segal, J. Chem. Soc.. Dalton Trans., 1677 (1975).
270. P. Bachmann, K.-R. Repp, and H. Singer, Z. Naturforsch. Teil B, 32, 471 (1977).
271. K. K. Bhasin, W. G. Balkeen, and P. L. Pauson, J . Organomet. Chem., 204,C25,(1981);
272. A. J. Pearson and I. C. Richards, J. Organomet. Chem., 258, C41 (1983).
273. A. Mawby, P. J. C. Walker, and R. J. Mawby, J.Organornet. Chem., 55, C39 (1973);
274. P. J. C. Walker and R. J. Mawby, Inorg. Chem., 10,404(1971);
275. P. J. C. Walker and R. J. Mawby Inorg. Chim. Acta, 7,621 (1973);
276. P. J. C. Walker and R. J. Mawby J . Chem. Soc. Dalton Trans., 622 (1973);
277. P. L. Pauson and J. L. Segal, J . Chem. Soc. Dalton Trans., 1683 (1975);
278. G .A. M. Munro and P. L. Pauson, Isr. J . Chem., 15, 258 (1976/77).
279. Y. K. Chung, H. S. Choi, and D. A. Sweigart ,J.Am. Chem. Soc., 104,4245(1982);
280. Y. K.Chung, P. G. Willard, and D. A. Sweigart, Organornetallics, I, 1053 (1982).
281. D. Astruc, Tetrahedron, 39, 4027 (1983).