Selective synthesis of cyclododec-2-en-1-yl ethers via palladium-catalyzed allylic substitution reaction: a kinetic study
The palladium-catalyzed reaction between isomeric cyclododec-2-en-1-yl acetates and primary aliphatic alcohols was found to result in high yields of the reaction products obtained. The selectivity with respect to cyclododec-2-en-1-yl ethers formed as reaction products ranged from 73% to 93%. The kinetics of the reaction of acetoxycyclododec-2-enes with alcohols was studied within the temperature range of 328--358 K. A kinetic equation best fitting the experimental data was provided.
Selective synthesis of cyclododec-2-en-1-yl ethers via palladium-catalyzed allylic substitution reaction: a kinetic study
The palladium-catalyzed reaction between isomeric cyclododec-2-en-1-yl acetates and primary aliphatic alcohols was found to result in high yields of the reaction products obtained. The selectivity with respect to cyclododec-2-en-1-yl ethers formed as reaction products ranged from 73% to 93%. The kinetics of the reaction of acetoxycyclododec-2-enes with alcohols was studied within the temperature range of 328--358 K. A kinetic equation best fitting the experimental data was provided.
___
- DE Patent 2 152 016, Chem. Abstr. 77, 1972, 47952s.
- DE Patent 2 928 348, Chem. Abstr. 95, 1981, 6637w.
- EU Patent 95 611 A1, Chem. Abstr. 100, 1984, 191436n.
- RF Patent 979 321, Ref. Zh. Khim. 1983, 20H117 (Russ.).
- Tsuji, J. Palladium Reagents and Catalysts, John Wiley & Sons Ltd: Chichester, UK, 1998, pp. 560. Bao, M.; Nakamura, H.; Inoue, A.; Yamamoto, Y. Chem. Lett. 2002, 2, 158–159.
- Wallner, O. A.; Szabo, K. J. J. Org. Chem. 2003, 68, 2934–2943.
- Arthuis, M.; Beaud, R.; Gandon, V.; Roulland, E. Angew. Chem. Int. Ed. 2012, 51, 10510–10514.
- Sigismond, S.; Sinou, D., J. Mol. Catal. 1997, 116, 289–296.
- Dawson, G.; Williams J. Tetrahedron: Asymmetry 1995, 6, 2535–2546.
- Allen, J.; Coote, St.; Dawson, G.; Frost, Ch.; Martin, Ch.; Williams, J. J. Chem. Soc. Perkin Trans. 1994, 1, 2065–2072.
- Schmid, R.; Sapunov, V. N., Non-Formal Kinetics, Verlag Chemie, Basel, Switzerland, 1982.
- Kolev, As.; Skumov, M.; Balbolov, E. React. Kinet. Catal. Lett. 2003, 7, 8325–8330.
- Coulson, D. Inorganic Syntheses XIII, 1972, 121.
- Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jap. 1972, 45, 230–236.
- Kamenski, D. I.; Dimitrov, S. D. Computers Chem. Engng. 1993, 17, 643–651.
- Marquardt, D. W. J. Soc. Ind. Appl. Math. 1963, 11, 431–441.