Synthesis of O-(1-propenyl) monomers via ruthenium complex-catalyzed isomerization of allyl systems

A route was developed to synthesize di- and multi-functional O-(1-propenyl) monomers, primarily R-O-CH=CHCH3(R = Me3Si, (CH2CH)(2)OH, n =1, 2) and CH3CH=CH-O-Y-O-CH = CHCH3 (Y = -CH2-, -(CH2CH2)(n)- (n = 1, 2), CH2CH=CHCH2,-,1,2- and 1,3-C6H4. Si(OEt)(2)), involving isomerization of allyl, di- and multi-allyl ethers, allyl acetals and allyl esters. Systems Z(O-CH=CHCH3)(3) (Z = CH, B, PhCH, Si(OEt), 1,3,5-C6H3) were also prepared. Ru(II) complexes, primarily [RuCIH(CO)(PPh3)(3)] and [RuH2(PPh3)(4)], were used (reactant/Ru = 500) as homogeneous catalysts. Conversion of the allyl system was always quantitative, except for diallyl phthalate, where polymers were formed. A method was developed to recycle the catalyst for the model isomerization of 1,4-diallyloxybutane run in the presence of 0.2 mol% of [RuCIH(CO)(PPh3)(3)].