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Study on the reaction of 4-allyloxybutane-1-ol with ruthenium (II) complexes

Urbala M.

Polish Journal of Chemical Technology

2005

Vol. 7, nr 4

48-50

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.