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

Molecules. 2010 Jan 20;15(1):407-19. doi: 10.3390/molecules15010407.

Abstract

Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CH-CH(CH3)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, p-NO2) and 7-X-1,2-dihydronaphthalene derivatives (where X is H, MeO); FVP of 1-aryl-3-benzyloxy1-1-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-1-ylbenzene derivatives (ArCH2CH=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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis
  • Alcohols / chemistry*
  • Ethers / chemical synthesis
  • Ethers / chemistry*
  • Gases / chemistry*
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Temperature*

Substances

  • Alcohols
  • Ethers
  • Gases