Hydroformylation of myrcene: Metal and ligand effects in the hydroformylation of conjugated dienes

New Journal of Chemistry

Volumn 27, Issue 3, 2003, Pages 533-539

  Foca, Cláudia M ^a   Barros, Humberto J V ^b   Dos Santos, Eduardo N ^b   Gusevskaya, Elena V ^b   Bayón, J Carles ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

3 ETHYLIDENE 7 METHYL 6 OCTENAL; 4 METHYLENE 8 METHYL 7 NONENAL; ALDEHYDE; ALKADIENE; MYRCENE; PLATINUM; RHODIUM; TIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0037348482     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b207947j     Document Type: Article

References (60)

1. For recent reviews on the application of hydroformylation in fine chemistry see: S. Castillón and E. Fernández in Rhodium Catalyzed Hydroformylation, ed. P. W. N. M. van Leeuwen and C. Claver, Kluwer Academic Press, Dordrecht, 2000, p. 145; (b) B. Breit and W. Seiche, Synthesis, 2001, 1, 1; (c) P. Eilbracht, L. Bärfacker, C. Buss, C. Hollmann, B. E. Kitsos-Rzychon, C. L. Kranemann, T. Rische, R. Roggenbuck and A. Schmidt, Chem. Rev., 1999, 99, 3329.
2. For recent reviews on the application of hydroformylation in fine chemistry see: S. Castillón and E. Fernández in Rhodium Catalyzed Hydroformylation, ed. P. W. N. M. van Leeuwen and C. Claver, Kluwer Academic Press, Dordrecht, 2000, p. 145; (b) B. Breit and W. Seiche, Synthesis, 2001, 1, 1; (c) P. Eilbracht, L. Bärfacker, C. Buss, C. Hollmann, B. E. Kitsos-Rzychon, C. L. Kranemann, T. Rische, R. Roggenbuck and A. Schmidt, Chem. Rev., 1999, 99, 3329.
3. For recent reviews on the application of hydroformylation in fine chemistry see: S. Castillón and E. Fernández in Rhodium Catalyzed Hydroformylation, ed. P. W. N. M. van Leeuwen and C. Claver, Kluwer Academic Press, Dordrecht, 2000, p. 145; (b) B. Breit and W. Seiche, Synthesis, 2001, 1, 1; (c) P. Eilbracht, L. Bärfacker, C. Buss, C. Hollmann, B. E. Kitsos-Rzychon, C. L. Kranemann, T. Rische, R. Roggenbuck and A. Schmidt, Chem. Rev., 1999, 99, 3329.
4. (a) W. E. Erman, Chemistry of the Monoterpenes. An Encyclopedic Handbook, Marcel Dekker, New York, 1985;
5. (b) D. H. Grayson, Nat. Prod. Rep., 1988, 3, 419.
6. G. Fráter, J. A. Bajgrowicz and P. Kraft, Tetrahedron, 1998, 54, 7633.
7. (a) A. J. Chalk in Flavors and Fragances: A World Perspective, ed. B. M. Lawrence, B. D. Mookherjee and B. J. Willis, Elsevier Science, Amsterdam, 1988;
8. (b) I. Ciprés, Ph. Kalck, D.-C. Park and F. Serein-Spirau, J. Mol. Catal., 1991, 66, 399;
9. (c) L. Kollár and G. Bódi, Chirality, 1995, 1, 121;
10. (d) K. Soulantica, S. Sirol, S. Koinis, G. Pneumatikakis and Ph. Kalck, J. Organomet. Chem., 1995, 498, C10;
11. (e) F. Azzaroni, P. Biscarini, S. Bordoni, G. Longoni and E. Venturini, J. Organomet. Chem., 1996, 508, 59;
12. (f) S. Sirol and Ph. Kalck, New J. Chem., 1997, 21, 1129.
13. (a) H. Siegel and W. Himmele, Angew. Chem., Int. Ed. Engl., 1980, 19, 178;
14. (b) A. J. Chalk, in Catalysis of Organic Reactions, ed. P. N. Rylander, H. Greenfield and R. L. Augustine, Marcel Dekker, New York, 1988, vol. 22, p. 43.
15. The Chemistry of Fragances, ed. D. H Pybus and C. S. Sell, RSC Paperbacks, Cambridge, 1999.
16. J. C. Chalchat, R. Ph. Garry, E. Lecomte and A. Michet, Flavour Fragrance J., 1991, 6, 178.
17. G. Liu and M. Garland, J. Organomet. Chem., 2000, 608, 76.
18. G. Natta and M. Beatti, Chim. Ind. (Milan), 1945, 27, 84.
19. H. Adkins and J. L. R. Williams, J. Org. Chem., 1952, 17, 980.
20. (a) B. Fell and H. Bahrmann, J. Mol. Catal., 1977, 7, 211;
21. (b) H. Bahrmann and B. Fell, J. Mol. Catal., 1980, 8, 329;
22. (c) B. Falk and B. Fell, J. Mol. Catal., 1983, 18, 127;
23. (d) P. W. N. M. van Leeuwen and C. F. Roobeek, Eur. Pat. Appl. 81-200033 to Shell, 1981;
24. (e) P. W. N. M. Van Leeuwen and C. F. Roobeek, J. Mol. Catal., 1985, 31, 345;
25. (f) C. Botteghi, M. Branca and A. Saba, J. Organomet. Chem., 1980, 184, C17;
26. (g) C. Botteghi, M. Branca and A. Saba, J. Organomet. Chem., 1987, 332, 229.
27. S. Bertozzi, N. Campigli, G. Vitulli, R. Lazzaroni and P. Salvadori, J. Organomet. Chem., 1995, 487, 41.
28. D. L. Packett, US 5,312,996 to Union Carbide, 1994.
29. Y. Ohgomori, N. Suzuki and N. Sumitani, J. Mol. Catal. A, 1998, 133, 289.
30. (a) T. Horiuchi, T. Ohta, K. Nozaki and H. Takaya, Chem. Commun., 1996, 155;
31. (b) T. Horiuchi, T. Ohta, E. Shirakawa, K. Nozaki and H. Takaya, Tetrahedron, 1997, 53, 7795.
32. (a) K. Osakada, J. C. Choi, T. Koimuzi, I. Yamaguchi and T. Yamamoto, Organometallics, 1995, 14, 4962;
33. (b) J. C. Choi, K. Osakada and T. Yamamoto, Organometallics, 1998, 17, 3044.
34. M. I. Dawson, P. D. Hobbs,Kuhlmann, V. A. Fung, C. T. Helmes and W. R. Chao, J. Med. Chem., 1980, 23, 1013.
35. (a) C. P. Casey and G. T. Whiteker, Isr. J. Chem., 1990, 30, 299;
36. (b) P. Dierkes and P. W. N. M. van Leeuwen, J. Chem. Soc., Dalton Trans., 1999, 1519.
37. M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer and P. W. N. M. van Leeuwen, Organometallics, 1995, 14, 3081.
38. (a) C. P. Casey, G. T. Whiteker, M. G. Melville, L. M. Petrovich, J. A. Gavney Jr. and D. R. Powell, J. Am. Chem. Soc., 1992, 114, 5535;
39. (b) P. W. N. M. van Leeuwen, G. J. H. Buisman, A. van Rooy and P. C. J. Kamer, Recl. Trav. Chim. Pays-Bas, 1994, 113, 61.
40. See reference 1a, chapters 3 and 4.
41. (a) E. L. Muetterties, Acc. Chem. Res., 1970, 3, 266;
42. (b) P. Meakin, E. L. Muetterties and J. P. Jesson, J. Am. Chem. Soc., 1972, 94, 5271.
43. C. P. Casey, G. T. Whiteker, C. F. Campana and D. R. Powell, Inorg. Chem., 1990, 29, 3376.
44. J. M. Brown and A. G. Kent, J. Chem. Soc., Perkin Trans. 2, 1987, 1597.
45. (a) C. Y. Hsu and M. Orchin, J. Am. Chem. Soc., 1975, 97, 3553;
46. (b) I. Schwager and J. F. Knifton, J. Catal., 1976, 45, 256;
47. (c) G. K. Anderson, H. C. Clark and J. A. Davies, Organometallics, 1982, 1, 64;
48. (d) M. Gómez, G. Muller, D. Sainz and J. Sales, Organometallics, 1991, 10, 4036;
49. (e) P. J. Stang, Z. Zhong and A. M. Arif, Organometallics, 1992, 11, 1017;
50. (f) I. Tóth, T. Kégl, C. J. Elseiver and L. Kollár, Inorg. Chem., 1994, 33, 5708;
51. (g) E. V. Gusevskaya, E. N. dos Santos, R. Augusti, A. O. Dias and C. M. Foca, J. Mol. Catal. A, 2000, 152, 15.
52. W. R. Rocha and W. B. de Almeida, Organometallics, 1998, 17, 1961.
53. R. Usón, L. A. Oro and J. Cabeza, Inorg. Synth., 1985, 23, 126.
54. G. Giordano and R. H. Crabtree, Inorg. Synth., 1979, 19, 218.
55. T. G. Devon, G. W. Phillips, T. A. Puckette, J. L. Stavinoa and J. J. Vanderbilt, US 4,694,109 to Texas Eastman, 1987.
56. E. Billig, A. G. Abatjoglou and D. R. Bryant, US 4,668,651 to Union Carbide, 1987.
57. M. Camalli, F. Caruso, S. Chaloupka, E. M. Leber, H. Rimml and L. M. Venanzi, Helv. Chim. Acta, 1990, 73, 2263.
58. K. C. Eapen and C. Tamborski, J. Fluorine Chem., 1980, 15, 239.
59. P. W. N. M. van Leeuwen and C. F. Roobeek, J. Organomet. Chem., 1983, 258, 343.
60. M. Behforouz, J. L. Bolan and M. S. Flynt, J. Org. Chem., 1985, 50, 1186.