Homogeneous and biphasic nickel-catalyzed isomerization of allylic alcohols

European Journal of Inorganic Chemistry

Volumn , Issue 11, 1998, Pages 1739-1744

  Bricout, Hervé ^a   Monflier, Eric ^a   Carpentier, Jean François ^b   Mortreux, André ^b  

^a UNIVERSITÉ D'ARTOIS   (France)

^b UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

Author keywords

Allylic alcohol; Homogeneous catalysis; Isomerization; Nickel; Two phase catalysis

Indexed keywords

CATALYST DEACTIVATION; COORDINATION REACTIONS; ISOMERIZATION; ISOMERS; NICKEL COMPOUNDS;

ALLYLIC ALCOHOL; CATALYSTS DEACTIVATION; HOMOGENEOUS CATALYSIS; HOMOGENEOUS PHASE; HOMOGENEOUS SYSTEM; ISOMERISATION; NICKEL SPECIES; TWO PHASE; TWO PHASE SYSTEMS; TWO-PHASE CATALYSE;

CATALYSIS;

EID: 0002518002     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0682(199811)1998:11<1739::AID-EJIC1739>3.0.CO;2-I     Document Type: Article

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6. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
7. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
8. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
9. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
10. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
11. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
12. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
13. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
14. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
15. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
16. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d] F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
17. Isomerization of allylic alcohols proceeds with many other transition metal catalysts; Molybdenum: [4a] Y. Lin, X. Lu. J. Organomet. Chem. 1983, 251, 321-325. - Iron: [4b] G. F. Emerson, R. Pettit, J. Am. Chem. Soc. 1962, 84, 4591-4592. [4c] R. Damico, T. J. Logan, J. Org. Chem. 1967, 32, 2356-2358. [4d]F. G. Cowherd, J. L. von Rosenberg, J. Am. Chem. Soc. 1969, 91. 2157-2158. - Rhodium: [4e] W. Strohmeier, L. Weigelt, J. Organomet. Chem. 1975, 86, C17-C19. [4f] C. Botteghi, G. Giacomelli, Gazz. Chim. Ital 1976, 106, 1131-1134. [4g] H. Alper, K. Hachem, J. Org. Chem. 1980, 45, 2269-2270. [4h] M. Kitamura, K. Manabe, R Noyori, H. Takaya, Tetrahedron Lett. 1987, 28, 4719-4720. [4i] J. Park , C. S. Chin, J. Chem Soc., Chem. Commun 1987, 1213-1214. [4j] S. H. Bergens, B. Bosnich, J. Am. Chem. Soc 1991, 113, 958-967. [4k] A. M. Trzeciak, J. J. Ziolkowski, Gazz. Chim. Ital 1994, 124, 403-409. - Iridium: [4l] D. Baudry, M. Ephritikhine, H. Felkin, New J. Chem. 1978, 2, 355-356. [4m] C. S. Chin, J. Park, C. Kim, S. Y. Lee, J. H. Shin, J. B. Kim, Catal. Lett. 1988, 1, 203-206.
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