127558-48-9Relevant academic research and scientific papers
Acid-catalyzed solvolysis of polyenol ethers. III. Effect of the alkoxy moiety
Nieuwenhuis, Saskia A. M.,Vertegaal, Louis B. J.,De Zoete, Marian C.,Van Der Gen, Arne
, p. 13207 - 13230 (2007/10/02)
The dependence of the solvolysis of polyenol ethers on the nature of the alkoxy moiety has been studied. A new reaction path, leading to the formation of ω-hydroxy (methoxy) substituted aldehydes and -esters, was established. The proposed reaction pathway (scheme 6) is initiated by an electron transfer from the polyenol ether to molecular oxygen, followed by combination of the two radicals to a peroxide zwitterion. Upon protonation, solvent adds to the ω-carbon atom of the polyene to give an intermediate that can either loose water to form an ester, or loose the alkoxy moiety to give an aldehyde. This mechanism is believed to be involved in the strong mutagenic activity displayed by many polyenol ethers, including the natural mutagen fecapentaene-12.
ANOMALOUS SOLVOLYSIS OF A POLYENOL ETHER OF GLYCEROL
Vertegaal, L. B. J.,Steeg, M. Van Der,Gen, A. Van Der
, p. 5639 - 5642 (2007/10/02)
Fecapentaene-12 1 displays an unexpected reactivity when treated with hydrochloric acid in aqueous solvents.Instead of forming the unsubstituted aldehyde 2,4,6,8-dodecatetraenal 2, a completely different pathway is observed, resulting in the exclusive formation of 10-methoxy-2,4,6,8-dodecatetraenal 3a (methanol/water) or 10-hydroxy-2,4,6,8-dodecatetraenal 3b (tetrahydrofuran/water).
