99187-38-9Relevant academic research and scientific papers
Reductive cleavage versus hydrogenation of allyl aryl ethers and allylic esters using sodium borohydride/catalytic ruthenium(III) in various aqueous solvent mixtures
Babler, James H.,White, Nicholas A.,Kowalski, Eric,Jast, Jeffrey R.
experimental part, p. 745 - 748 (2011/03/21)
The reduction of allyl aryl ethers using sodium borohydride in the presence of a catalytic amount of ruthenium(III) chloride in various aqueous solvent mixtures at 0 °C was examined. In aqueous tetrahydrofuran, hydrogenation was the favored pathway (85-100% yield of the corresponding aryl propyl ether); whereas in aqueous N-methylformamide, reductive cleavage predominated (4:1 mixture of phenolic product/aryl propyl ether). In order to gain some insight into the mechanism for this process, 3-octyn-1-ol and trans-2-decen-1-yl acetate were subjected to similar reductive conditions; and both substrates afforded products inconsistent with a single-electron-transfer mechanism.
