Isomerization of allyl aryl ethers to their 1-propenyl derivatives catalysed by ruthenium complexes

Journal of Molecular Catalysis A: Chemical

Volumn 219, Issue 1, 2004, Pages 29-40

  Krompiec, Stanisław ^a   Kuźnik, Nikodem ^a   Penczek, Robert ^a   Rzepa, Józef ^b   Mrowiec Białoń, Julita ^c  

^a SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF SILESIA   (Poland)

^c INSTITUTE OF CHEMICAL ENGINEERING   (Poland)

Author keywords

1 propenyl ethers; Allyl ethers; Double bond migration; Isomerization; Ruthenium complexes; Siliceous mesoporous cellular foams

Indexed keywords

CATALYST SELECTIVITY; CHEMICAL BONDS; DERIVATIVES; ETHERS; ISOMERIZATION; MESOPOROUS MATERIALS; REACTION KINETICS; RUTHENIUM; SOLVENTS;

ARYL ETHERS; SELECTIVITY CONTROL;

COMPLEXATION;

(4 AMINOPHENYL)(1 PROPENYL)ETHER; ALLYL COMPOUND; ETHER DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPYLENE; RUTHENIUM COMPLEX; SOLVENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CRYSTALLIZATION; DISTILLATION; ISOMERIZATION; QUANTITATIVE ANALYSIS; RACEMIC MIXTURE;

EID: 3042829020     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2004.04.039     Document Type: Article

References (66)

1. Taskinen E. J. Chem. Soc., Perkin Trans. 2(9):2001;1824
2. Bauld N.L., Aplin J.T., Yueh W., Endo S., Loving A. J. Phys. Org. Chem. 11:1998;15
3. Mereyala H.B., Gurrala S.R., Mohan S.K. Tetrahedron. 55:1999;11331
4. Carless H.A.J., Haywood D.J. J. Chem. Soc., Chem. Commun. 20:1980;980
5. Onishi M., Oishi S., Sakaguchi M., Takaki I., Hiraki K. Bull. Chem. Soc. Jpn. 59:1986;3925
6. Wille, S. Tomm, H. Frauenrath, Synthesis (1998) 305.
7. Bauld N.L., Yang J. Tetrahedron Lett. 40:1999;8519
8. Mereyala H.B., Lingannagaru S.R. Tetrahedron. 53:1997;17501
9. Kirmse W., Hoemberger G. J. Am. Chem. Soc. 113:1991;3925
10. Van Boeckel C.C.A.A., Boom J.H. Tetrahedron Lett. 20:1979;3561
11. Boons G.-J., Isles S. Tetrahedron Lett. 35:1994;3593
12. Cadot C., Dalko P.I., Cossy J. Tetrahedron Lett. 43:2002;1839
13. Karlen T., Ludi A. Helv. Chim. Acta. 75:1992;1604
14. Becker E., Slugovc C., Ruba E., Standfest-Hauser C., Mereiter K., Schmid R., Kirchner K. J. Organomet. Chem. 649:2002;55
15. Salvini A., Frediani P., Piacenti F. J. Mol. Catal. A: Chem. 159:2000;185
16. Crivello J.V., Kong S. J. Polym. Sci., Part A: Polym. Chem. 37:1999;3017
17. Malanga C., Menicagli R., Dell'Innocenti M., Lardicci L. Tetrahedron Lett. 28:1987;239
18. Curran D.P., Jacobs P.B., Elliott R.L., Kim B.H. J. Am. Chem. Soc. 109:1987;5280
19. Wakamatsu H., Nishida M., Adachi N., Mori M. J. Org. Chem. 65:2000;3966
20. Crivello J.V., Liu S.S. J. Polym. Sci., Part A: Polym. Chem. 36:1999;1199
21. Kaur S., Crivello J.V., Pascuzzi N. J. Polym. Sci., Part A: Polym Chem. 37:1999;199
22. Krompiec S., Kuźnik N., Bieg T., Adamus B., Majnusz J., Grymel M. Pol. J. Chem. 74:2000;1197
23. Krompiec S., Suwiński J. Pol. J. Chem. 64:1990;505
24. Krompiec S., Suwiński J., Grobelny J. J. Mol. Catal. 89:1994;303
25. Krompiec S., Suwiński J., Gibas M., Grobelny J. Pol. J. Chem. 70:1996;133
26. Krompiec S., Suwiński J., Grobelny J., Wagner P. Pol. J. Chem. 71:1997;747
27. W.A.L. van Otterlo, R. Pathak, C.B. de Koning, Synlett (2003) 1859.
28. van Otterlo W.A.L., Ngidi E.L., de Koning C.B. Tetrahedron Lett. 44:2003;6483
29. B. Schmidt, Eur. J. Org. Chem. (2003) 816.
30. Sworen J.C., Pawlow J.H., Case W., Lever J., Wagener K.B. J. Mol. Catal. A: Chem. 194:2003;69
31. T. Saito, K. Maeda, S. Yamada, JP 09,143,897 (1997), C.A. 127 (1997) 110507.
32. Yamamoto K., Higashimura T. J. Polym. Sci., Part A: Polym. Chem. 12:1974;613
33. T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, second ed., Wiley, New York, 1991.
34. Beugelmans R., Bourdet S., Bigot A., Zhu J. Tetrahedron Lett. 35:1994;4349. (and the works cited therein)
35. Guibe F. Tetrahedron. 53:1997;13509
36. Hurd C.D., Greengard H., Pilgrim F.D. J. Am. Chem. Soc. 52:1930;1700
37. Bruce J.M., Roshan-Ali Y. J. Chem. Soc., Perkin Trans. 1:1981;2677
38. Goering H.L., Jacobson R.R. J. Am. Chem. Soc. 80:1958;3277
39. S. Oishi, N. Kuhara, A. Hosaka, Chem. Lett. (1985) 621.
40. G.W. Parshall, S.D. Ittel, Homogeneous catalysis, second ed., Wiley-Interscience, New York, 1992, pp. 9-24.
41. R.H. Crabtree, The Organometallic Chemistry of the Transition Metals, second ed., Wiley-Interscience, New York, 1994, pp. 210-212.
42. B. Cornils, A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds, vol. 2, Wiley-VCH, Weinheim, 2002, pp. 980-991.
43. McGrath D.V., Grubbs R.H. Organometallics. 13:1994;224
44. Krompiec S., Suwiński J., Grobelny J. Pol. J. Chem. 70:1996;813
45. S. Krompiec, Isomerization of alkenes and their functionally substituted derivatives catalyzed by ruthenium complexes, Zesz. Nauk. Pol. Sl. 1 136 (1997) 1-174.
46. Krompiec S., Pigulla M., Bieg T., Szczepankiewicz W., KuŸnik N., Krompiec M., Kubicki M. J. Mol. Catal. A: Chem. 189:2002;169
47. Krompiec S., Pigulla M., Szczepankiewicz W., Bieg T., Kuźnik N., Leszczyńska-Sejda K., Kubicki M., Borowiak T. Tetrahedron Lett. 42:2001;7095
48. Kuźnik N., Krompiec S., Bieg T., Baj S., Skutil K., Chrobok A. J. Organomet. Chem. 665:2003;167
49. Tolman C.A. Chem. Rev. 77:1977;313
50. Yanlong Q., Junming Z., Jiaqi L., Qichen H., Weihua X., Shoushan C. J. Mol. Catal. 38:1986;331
51. Frauenrath H., Runsink J. J. Org. Chem. 52:1987;2707
52. A. Pross, Theoretical and Physical Principles of Organic Reactivity, Wiley, New York, 1995, pp. 160-172.
53. Foltynowicz Z., Krompiec S., Wagner P., Maciejewski H. Pol. J. Chem. 70:1996;468
54. J.J. Levison, S.D.J. Robinson, J. Chem. Soc. A (1970) 2947.
55. Ahmad N., Levison J.J., Robinson S.D., Uttley M.F. Inorg. Synth. 15:1974;45
56. T.A. Stephenson, G. Wilkinson, J. Chem. Soc. A (1968) 2660.
57. E.W. Abel, M.A. Bennett, G. Wilkinson, J. Chem. Soc. A (1959) 3178.
58. Young R., Wilkinson G. Inorg. Synth. 17:1977;75
59. E.W. Abel, M.A. Bennett, G. Wilkinson, J. Chem. Soc. A (1959) 3178.
60. J. Chatt, L.M. Venanzi, J. Chem. Soc. (1957) 4735.
61. McKillop A., Fiaud J.C., Hug R.P. Tetrahedron. 30:1974;1379
62. Claisen L., Eisleb O. Just. Lieb. Ann. Chem. 401:1913;59
63. Wilson W.C., Adams R. J. Am. Chem. Soc. 45:1923;538
64. Wang Z.M., Zhang X.L., Sharpless K.B. Tetrahedron Lett. 34:1993;2267
65. Schmidt-Winkel P., Lukens W.W. Jr., Zhao D., Yang P., Chmelka B.F., Stucky G.D. J. Am. Chem. Soc. 121:1999;254
66. Schmidt-Winkel P., Lukens W.W. Jr., Yang P., Margolese D.I., Lettow J.S., Ying J.Y., Stucky G.D. Chem. Mater. 12:2000;686