Abstract
Olefin insertions into transition metal-carbon and transition metal-hydrogen bonds are fundamental reactions in homogeneous catalysis. With unsymmetrically substituted olefins, a remarkable regioselectivity is frequently observed, whereby the orientation of the olefin depends on the metal, the ligands, and the olefin itself. Empirical rules of regioselectivity are given, and interpreted on the base of the electronic structure of the reaction partners.
Present address: Monsanto Triangle Park Development Center Inc., P.O. Box 12274, Research Triangle Park, N.C. 27709, U.S.A.
Preview
Unable to display preview. Download preview PDF.
References
Roelen, O.: Angew. Chem. 60, 62 (1948).
Smidt, J., Hafner, W., Jira, R., Sedlmeier, J., Sieber, R., Rüttinger, R., and Kojer, H.: Angew. Chem. 71, 176 (1959); Jira, R., Sedlmeier, J., Smidt, J.: Justus Liebigs Ann. Chem. 693, 99 (1966).
Barlow, M. C., Bryant, M. J., Haszeldine, R. N., Mackie, A. G.: J. Organometal. Chem. 21, 215 (1970); Henrici-Olivé, G., Olivé, S.: Angew. Chem. 87, 110 (1975); Angew. Chem. Internat. Edit. 14, 104 (1975).
Henrici-Olivé, G., Olivé, S.: Adv. Polymer Sci. 15, 1 (1974), and references therein.
Markownikoff, V. W.: Compt. rend. 81, 668 (1875).
Pople, J. A., Gordon, M.: J. Amer. Chem. Soc. 89, 4253 (1967).
Churchill, M. R., Mason, R.: Adv. Organometal. Chem. 5, 93 (1967).
Armstrong, D. R., Perkins, P. G., Stewart, J. J. P.: J. C. S. Dalton, 1972, 1972.
e.g.: Ballhausen, C. J., Gray, H. B.: Inorg. Chem. 1, 111 (1962); Dutta-Ahmed, A., and Boudreaux, E. A.: Inorg. Chem. 12, 1597 (1973).
Novaro, O., Chow, S., Magnouat, P.: J. Catal. 41, 91 (1976).
Parshall, G. W., Mrowca, J. J.: Adv. Organometal. Chem. 7, 157 (1968).
Lappert, M. F., Patil, D. S., Pedley, J. B.: J. C. S. Chem. Commun. 1975, 830.
Yamazaki, H., Nishido, T., Matsumoto, Y., Sumida, S., Hagihara, N.: J. Organometal. Chem. 6, 86 (1966).
Zambelli, A., Tosi, C.: Adv. Polymer Sci. 15, 31 (1974).
Kaesz, H. D., Saillant, R. B.: Chem. Rev. 72, 231 (1972).
Henrici-Olivé, G., Olivé S.: Angew. Chem. 80, 398 (1968); Angew. Chem. Internat. Edit. 7, 386 (1968).
Brintzinger, H. H.: J. Amer. Chem. Soc. 89, 6871 (1967).
Henrici-Olivé, G., Olivé, S.: Chem. Commun. 1969, 1482.
Buckingham, A. D., Stephens, P. J.: J. Chem. Soc. 1964, 2747, and references therein.
Stevens, R. M., Kern, C. W., Lipscomb, W. N.: J. Chem. Phys. 37, 279 (1962).
Lohr, L. L., Lipscomb, W. N.: Inorg. Chem. 3, 22 (1964).
Armstrong, D. R., Fortune, R., Perkins, P. G.: J. Catalysis 41, 51 (1976).
Schunn, R. A., in: Transition metal hydrides (E. L. Muetterties, ed.), p. 203. New York; Marcel Dekker, Inc. 1971.
Chatt, J., Hayter, R. G.: J. Chem. Soc. 1963, 6017.
Appleton, T. G., Clark, H. C., Manzer, L. E.: Coord. Chem. Rev. 10, 335 (1973).
Adams, D. M., Chatt, J., Shaw, B. L.; J. Chem. Soc. 1960, 2047.
Chatt, J., Duncanson, L. A., Shaw, B. L., Venanzi, L. M.: Disc. Farad. Soc. 26, 131 (1958).
Edgell, W. F., Gallup, G.: J. Amer. Chem. Soc. 78, 4188 (1956).
Falbe, J.: Synthesen mit Kohlenmonoxyd. Berlin-Heidelberg-New York: Springer 1967; Carbon monoxide in organic synthesis (translated by.C. R. Adams). Berlin-Heidelberg-New York: Springer 1970.
Taft, R. W., Deno, N. C., Skell, P. S.: Ann. Rev. Phys. Chem. 9, 287 (1958); see also J. Amer. Chem. Soc. 85, 3146 (1963).
Coulson, C. A., Streitwieser, A.: Dictionary of π-electron calculations, in: Streitwieser, A., Brauman, J. I.: Supplemental tables of MO calculations, Vol. 2. Oxford: Pergamon Press 1965.
Gey, E.: Z. Chem. 11, 392 (1971).
Houk, K. N., Munchausen, L.: J. Amer. Chem. Soc. 98, 937 (1976).
Houk, K. N.: J. Amer. Chem. 95, 4092 (1973), and references therein.
Sustmann, R., Trill, H.: Angew. Chem. 84, 887 (1972); Angew. Chem. Internat. Edit. 11, 838 (1972).
O'Neal, H. E., Benson, S. W.: J. Phys. Chem. 71, 2903 (1967).
Cramer, R.: J. Amer. Chem. Soc. 87, 4717 (1965).
See, e.g.:Ashcroft, S. J., Mortimer, C. T.: J. Chem. Soc. A, 1967, 930; Egger, K. W.: J. Organometal. Chem. 24, 501 (1970); Telnoi, V. I., et al.: Dokl. Akad. Nauk SSSR 174, 1374 (1967).
Cramer, R.: J. Amer. Chem. Soc. 94, 5681 (1972).
Cotton, F. A., Wilkinson, G.: Advanced inorganic chemistry. New York: Interscience Publ. 1966.
Stefani, A., Consiglio, G., Botteghi, C., Pino, P.: J. Amer. Chem. Soc. 95, 6504 (1973).
Noack, K., Calderazzo, F.: J. Organometal. Chem. 10, 101 (1967).
Cossee, P.: J. Catalysis 3, 80 (1964)
Cossee, P.: Rec. Trav. Chim., Pays-Bas, 85, 1151 (1966).
Nakamura, A., Otsuka, S.: J. Amer. Chem. Soc. 94, 1886 (1972).
Ariyaratne, J. K. P., Green, M. L. H.: J. Chem. Soc. 1963, 2976.
Chiusoli, G. P.: Accounts Chem. Res. 6, 422 (1973).
Otsuka, S., Nakamura, A., Yoshida, T., Naruto, M., Ataka, K.: J. Amer. Chem. Soc. 95, 3180 (1973).
Dewhurst, K. C.: Inorg. Chem. 5, 319 (1966).
Heck, R. F.: J. Amer. Chem. Soc. 91, 6707 (1969).
Heck, R. F.: J. Organometal. Chem. 37, 389 (1972).
Takegami, Y., Suzuki, T., Okazaki, T.: Bull. Chem. Soc. (Japan) 42, 1060 (1969).
Longi, P., Mazzanti, G., Roggero, A., Lachi, A. M.: Makromol. Chem. 61, 63 (1963).
de Vries, H.: Rec. trav. chim. 80, 866 (1961).
Bestian, H., Clauss, K.: Angew. Chem. 75, 1068 (1963); Angew. Chem. Internat. Edit 2, 704 (1963).
Shilov, A. E., Shilova, A. K., Bobkov, B. N.: Vysokomolekul. Soedin. 4, 1688 (1962).
Taylor, P., Orchin, M.: J. Amer. Chem. Soc. 93, 6504 (1971).
Bönnemann, H., Grard, Ch., Kopp, W., Wilke, G.: XXIIIrd. Internat. Congress of Pure and Appl. Chemistry, Boston 1971, Vol. 6, p. 265.
Henrici-Olivé, G., Olivé, S.: Transition Met. Chem., in press.
Phung, N. H., Lefebvre, G.: Compt. Rend. 265, 519 (1967).
Henrici-Olivé, G., Olivé, S., Schmidt, E.: J. Organometal. Chem. 39, 201 (1972).
Herberhohl, M.: Metal π-Complexes; Elsevier 1972.
Armstrong, D. R., Fortune, R., Perkins, P. G.: Inorg. Chim. Acta 9, 9 (1974).
Bogdanović, B., Henc, B., Karmann, H. G., Nüssel, H. G., Walter, D., Wilke, G.: Ind. Eng. Chem. 62, No. 12, 34 (1970).
Ewers, J.: Angew. Chem. 78, 593 (1966); Angew. Chem. Internat. Edit 5, 584 (1966).
Japanese Patent 72,24523 (1972).
U.S. Patent 3,651,111 (1972).
Bogdanovic, B.: Angew. Chem. 85, 1013 (1973); Angew. Chem. Internat Edit. 12, 954 (1973).
Misono, A., Uchida, Y., Tamai, K., Hidai, M.: Bull. Chem. Soc. Japan, 40, 931 (1967).
Misono, A., et al.: Chem. Commun. 1967, 357; 1968, 704.
Alderson, T., Jenner, E. L., Lindsey, R. V.: J. Amer. Chem. Soc. 87, 5638 (1965).
Trocha-Grimshaw, J., Henbest, H. B.: Chem. Commun. 1967, 544.
McPartlin, M.; Mason, R.: Chem. Commun. 1967, 545; J. Chem. Soc. (A), 1970, 2206.
Deeming, A. J., Johnson, B. F. G., Lewis, J.: J. C. S. Dalton 1973, 1848.
Chatt, J., Shaw, B. L.: J. Chem. Soc. 1962, 5075.
Clark, H. C., Kurosawa, H.: Inorg. Chem. 11, 1275 (1972).
Lodewijk, E., Wright, D.: J. Chem. Soc. (A) 1968, 119.
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1976 Springer-Verlag
About this paper
Cite this paper
Henrici-Olivé, G., Olivé, S. (1976). Olefin insertion in transition metal catalysis. In: Preparative Organic Chemistry. Topics in Current Chemistry, vol 67. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0048499
Download citation
DOI: https://doi.org/10.1007/BFb0048499
Received:
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-07900-2
Online ISBN: 978-3-540-38041-2
eBook Packages: Springer Book Archive