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Abstrakty
The allyl ether systems undergo double-bond isomerization to 1-propenyl ethers in the presence of phosphine ruthenium (II) complexes very smoothly and effectively. However, when functionally substituted allyl ether derivatives are used as the substrates, the course of the reaction of the substrate with a metal complex is substantially determined by the complexing ability of the functional group. The reaction of allyl substrates containing primary hydroxyl group (allyloxyalcohols) with phosphine ruthenium (II) complexes (i.e. [RuClH(CO)(PPh3)3], [RuCl2(PPh3)3]) has been investigated. It was found that this reaction leads selectively to either 1-propenoxy alcohols or to cyclic 2-ethyl-[1,3] acetals, depending on the complex used as a catalyst and the reaction conditions. For the model isomerization of 4-allyloxybutan-1-ol, the optimal parameters for highly selective and efficient synthesis of 4-(1-propenyloxy)butan-1-ol or 2-ethyl-[1,3]dioxepane are established.
Czasopismo
Rocznik
Tom
Strony
48--50
Opis fizyczny
Bibliogr. 16 poz., tab.
Twórcy
autor
- Szczecin University of Technology, Institute of Organic Chemical Technology, ul. Pułaskiego 10, 70-322 Szczecin
Bibliografia
- (1) Decker C.: Photoinitiated crosslinking polymerization, Prog. Polym. Sci., 1996, 21, 593 - 650.
- (2) Decker C., Biachini C., Decker D., Morel F.: Photoinitiated polymerization of vinyl ether-based systems, Prog. Org. Coat., 2001, 42, 253 - 266.
- (3) Sangermano M., Malucelli G., Bongiovanni R., Priola A., Annby U., Rehnberg N.: Cationic photoinitiated coplymerization of 1-propenyl-vinyl ether systems, Eur. Polym. J. 2002, 38, 655 - 659.
- (4) Crivello J., Jo K.: Propenyl ethers. I. The synthesis of propenyl ether monomers, J. Polym. Sci. Part A: Polym. Chem., 1993, 31, 1473 - 1482.
- (5) Rajaraman S., Crivello J.: Tandem isomerization/cationic polymerization of allylic ethers, Polym. Mater. Sci. Eng., 1997, 77, 603 - 604.
- (6) Martysz D., Urbala M., Antoszczyszyn M.: 1-Propenyl ethers of butanediol as effective modifiers of UV-cured epoxy coatings in cationic polymerization, Polimery, 2002, 47, 11 - 12, 849.
- (7) Kubisa P., Penczek S.: Cationic activated monomer polymerization of heterocyclic monomers, Prog. Polym Sci., 1999, 24, 1409 - 1437.
- (8) Sangermano M., Malucelli G., Bongiovanni R., Priola A., Annby U., Rehnberg N.: Cationic photoplymerization of polyfunctional 1-propenyl ether systems, Polym. Int. 2001, 50 (9), 998 - 1003.
- (9) Crivello J. V., Liu S.: Photoinitiated cationic polymerization of epoxy alcohol monomers, J. Polym. Sci.Part A: Polym. Chem. 2000, 38, 389 - 401.
- (10) Urbala M., Kuźnik N., Krompiec S., Antoszczyszyn M., Martysz D.: Przem. Chem. 2003, 82 (8 - 9) 642 - 644.
- (11) Urbala M., Antoszczyszyn M., Krompiec S.: Polish J. Chem. Tech. 2001, 3, 22 - 24.
- (12) Crivello J., Yang Bo, Kim Whan-Gi: Chemoselective hydrosilations. I. Synthesis and photopolymerization of 1-ropenyl ether functionalized siloxanes, J. Polym. Sci. Part A: Polym. Chem., 1995, 33, 2415 - 2423.
- (13) Prosser T. J.: The rearrangement of allyl ethers to propenyl ethers, J. Am. Chem. Soc, 1961, 83, 1701 - 1704.
- (14) Urbala M., Kuźnik N., Krompiec S., Rzepa J.: Highly selective isomerization of allyloxyalcohols to cyclic acetals or 1-propenyloxyalcohols, Synlett, in press.
- (15) Janus E., Antoszczyszyn M., Urbala M.: Synthesis of mono-and diallyl ethers of 1,4-dihydroxybutane, (Z)-l,4-dihydroxy-2-butene and l,4-dihydroxy-2-butyne, Polish J. Appl. Chem., 1999,43, 77 - 83.
- (16) Houghton R. P.: Kompleksy metali w chemii organicznej, PWN, Warszawa 1985.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BPS2-0035-0066
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