Gas-phase pyrolytic reaction of 4-Aryl-3-buten-2-ols and allyl benzyl ethers: Kinetic and mechanistic study

Abstract

Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CHCH(CHs)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO2] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH2, where Ar is Ph, p-MeO, p-Me, p-Cl, pNO2) and 7-×-1,2-dihydronaphthalene derivatives (where X is H, MeO); FVP of 1-aryl-3benzyloxyl-1-butenes and benzyl cinnamyl ethers [ArCH=CHCH(X)OCH2Ph, where Ar is phenyl, p-MeO, p-Me, p-Cl, X is H, Me, Ph] gave the corresponding but-2-en-l-ylbenzene derivatives (ArCH 2CH=CH-X, where X is H, Me, Ph) together with benzaldehyde. The proposed mechanism of these pyrolytic transformations was supported by kinetic and product analysis.