Abstract
The reactivity of organic groups bonded to metals is an interesting study in itself, but it becomes particularly important when the ramifications to organic synthesis are considered. At its simplest, metal complex formation can be used to block a reactive site while comparatively harsh conditions are used at another part of the molecule. In more sophisticated cases, the bonding of an organic group to a metal can be used to modify reactivity and regiospecificity. The reactions described in this chapter may be used to modify the organic group in an organometallic reagent which is used in organic synthesis.
This is a preview of subscription content, log in via an institution to check access.
Preview
Unable to display preview. Download preview PDF.
References
Ayrey, G., Brasington, R. D., and Poller, R. C. (1972). J. organomet. Chem. 35, 105
Birch, A. J., and Jenkins, I. D. (1976). In Transition Metal Organometallics in Organic Synthesis, Vol. 1 (H. Alper, ed.). Academic Press, New York, p. 1
Bursten, B. E., and Fenske, R. F. (1979). Inorg. Chem. 18, 1760
Bury, A., Ashcroft, M. R., and Johnson, M. D. (1978). J. Am. chem. Soc. 100, 3217
Ceccon, A., and Sartori, S. (1973). J. organomet. Chem. 50, 161
Cerichelli, G., Illuminati, G., Ortaggit, G., and Guilani, A. M. (1977). J organomet. Chem. 127, 357
Churchill, M. R. (1965). J. organomet. Chem. 4, 258
Churchill, M. R., and Mason, R. (1964). Proc. R. Soc. A 279, 191
Clark, H. C., Ibbott, D. G., Payne, N. C., and Shaver, A. (1975). J. Am. chem. Soc. 97, 3555
Colvin, E. W. (1981). Silicon in Organic Synthesis. Butterworth, London, p. 15
Cook, M. A., Eaborn, C., and Walton, D. R. M. (1970). J. organomet. Chem. 24, 301
Dauben, H. J., and Honnen, L. R. (1958). J. Am. chem. Soc. 80, 5570
Davidsohn, W., and Henry, M. C. (1966). J organomet. Chem. 5, 29
Davies, S. G., Green, M. L. H., and Mingos, D. M. P. (1978). Tetrahedron 34, 3047
Dublitz, D. E., and Rinehart, K. L. (1969). Org. React. 17, 1
Eaborn, C., and Webster, D. E. (1960). J. chem. Soc. 179
Efraty, A., and Maitlis, P. M. (1967). J. Am. chem. Soc. 89, 3744
Eyer, M., Schlögl, K., and Schölm, R. (1981). Tetrahedron 37, 4239
Fischer, E. O., and Herberich, G. E. (1961). Chem. Ber. 94, 1517
Fischer, E. O., Von Foerster, M., Kreiter, C. G., and Schwarzhans, K. E. (1967). J. organomet. Chem. 7, 113
Fischer, E. O., Stückler, P., Beck, H.-J., and Kreissl, F. R. (1976). Chem. Ber. 109, 3089
Fleming, I. (1981). Chem. Soc. Rev. 10, 83
Freedman, L. D., and Doak, G. O. (1959). J. org. Chem. 24, 1590
Herberich, G. E. and Michelbrink, R. (1970). Chem. Ber. 103, 3615
Herberich, G. E., and Schwarzer, J. (1970). Chem. Ber. 103, 2016
Herberich, G. E., Engelke, C., and Pahlmann, W. (1979). Chem. Ber. 112, 607
Herberich, G. E., Greiss, G., and Heil, F. (1970). J. organomet. Chem. 22, 273
Jackson, W. R., and Jennings, W. B. (1969). J. chem. Soc. (B) 1221
Jarvie, A. W. P. (1970). Organomet. Chem. Rev. A 6, 153
Klopman, G., and Calderazzo, F. (1967). Inorg. Chem. 6, 977
Komarov, N. V., and Yarosh, O. G. (1971). Bull. Acad. Sci. USSR Div. ehem. Sci. 20, 1476
McBride, D. W., Pruett, R. L., Pitcher, E., and Stone, F. G. A. (1962). J. Am. chem. Soc. 84, 497
Mazerolles, P.,and Lesbre,M. (1959). C.r. hebd. Seanc. Acad. Sci., Paris 248, 2018
Minot, C., Importiere, A., and Dubac, J. (1976). Tetrahedron 32, 1523
Murphy, J., and Poller, R. C. (1982). Chem. Ind. (Lond.) 724
Nesmeyanov, A. N., Volkenau, N. A., Isaeva, L. S., Bolesova, I. N. (1968). Dokl. Chem. (Engl. Transi.) 183, 1042
Nicholls, B., and Whiting, M. C. (1959). J. chem. Soc. 551
Pauson, P. L. (1977). Pure appl. Chem. 49, 839
Pauson, P. L. (1980). J. organomet. Chem. 200, 207
Pearson, A. J. (1980). Acc. chem. Res. 13, 463
Pettit, R. (1975). J. organomet. Chem. 100, 205
Rausch, M. D., Moser, G. A., and Lee, W. A. (1979). Synth. React. inorg. metalorg. Chem. 9, 357
Rosenblum, M., and Abbate, F.W. (1966). J. Am. chem. Soc. 88, 4178
Schmidt, H. (1920). Justus Leibigs Annin Chem. 421, 174
Semmelhack, M. F., Hall, H. T., Farina, R., Yoshifugi, M., Clark, G., Bargar, T., Hirotsu, K., and Clardy, J. (1979). J. Am. chem. Soc. 101, 3535
Seyferth, D. (1962). Prog. inorg. Chem. 3, 129
Seyferth, D., and Evnin, A. B. (1967). J Am. chem. Soc. 89, 1468
Seyferth, D., Washburne, C. C., Attridge, C. J., and Yamamoto, K. (1970). J. Am. chem. Soc. 92, 4405
Simmoneaux, G., and Jaouen, G. (1979). Tetrahedron 35, 2249
Slocum, D. W., and Ernst, C. R. (1970). Organomet. Chem. Rev. A 6, 337
Sommer, L. H., Tyler, L. J., and Whitmore, F. C. (1948). J. Am. chem. Soc. 70, 2872
Sommer, L. H., Bailey, D. L., Goldberg, G. M., Buck, C. E., Bye, T. S., Evans, F. J., and Whitmore, F. C. (1954). J. Am. chem. Soc. 76, 1613
Tsutsui, M., and Courtney, A. (1977). Adv. organomet. Chem. 16, 241
Vyazankin, N. S., Gladyshev, E. N., and Razuvaev, G. A. (1963). Dokl. Chem. (Engl. Transl.) 153, 878
Whitla, W. A., Powell, H. M., and Venanzi, L. M. (1966). Chem. Commun. 310
Whitmore, F. C., and Sommer, L. H. (1946). J. Am. chem. Soc. 68, 481
General Reading
Barnett, K. W. (1974). The chemistry of nickelocene. J. organomet. Chem. 78, 139
Deganello, G. (1979). Transition Metal Complexes of Cyclic Polyolefins. Academic Press, New York
Efraty, A. (1977). Cyclobutadienemetal complexes. Chem. Rev. 71, 691
Leonova, E. V., and Kochetkova, N. S. (1973). Chemical reactions of cobaltocene and nickelocene. Russ. Chem. Rev. (Engl. Transl.) 42, 278
Rosenblum, M. (1965). Chemistry of the Iron Group Metallocenes: Ferrocene, Ruthenocene and Osmocene. Wiley, New York
Semmelhack, M., Clark, G. R., Garcia, J. L., Harrison, J. J., Thebtaranonth, Y., Wulf, W., and Yamashita, A. (1981). Addition of carbon nucleophiles to arene-chromium complexes. Tetrahedron 37, 3957
Sheats, J. E. (1979). The chemistry of cobaltocene, cobalticinium salts and other cobalt sandwich compounds. J. organomet. Chem. Library 7, 461
Author information
Authors and Affiliations
Copyright information
© 1986 A. W. Parkins and R. C. Poller
About this chapter
Cite this chapter
Parkins, A.W., Poller, R.C. (1986). Reactions of Organic Groups Bonded to Metals in Which the Metal — Carbon Bond is Retained. In: An Introduction to Organometallic Chemistry. Palgrave, London. https://doi.org/10.1007/978-1-349-18198-8_5
Download citation
DOI: https://doi.org/10.1007/978-1-349-18198-8_5
Publisher Name: Palgrave, London
Print ISBN: 978-0-333-36433-8
Online ISBN: 978-1-349-18198-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)