Effect of the. beta. substituent of the allylic unit in o- and p-cresol ethers on the mechanism of thermal and catalytic rearrangements
It is known that the catalytic rearrangement of the ..beta..-methylallyl ethers of phenols takes place by an intramolecular mechanism involving a (3,3)-sigmatropic shift. It was shown for the case of 1,1-bix ((2-methylphenoxy)methyl)ethene and 1,1-bis((4-methylphenoxy)methyl)ethene that substitution of a hydrogen atoms in the methyl group at the ..beta.. position of the allylic unit in the ethers of o- and p-cresols by a tolyloxy group leads to an intermolecular catalytic rearrangement. Only one O-C bond takes part in the reaction with subsequent cyclization of the obtained phenol ether to coumaran. The thermal rearrangement of such ethers takes place by an intramolecular mechanism with the subsequent involvement of both O-C bonds.
- Research Organization:
- Lensovet Leningrad Technological Institute (USSR)
- OSTI ID:
- 6364643
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:7; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
Similar Records
Rearrangement of oxime allyl ethers under electronic impact
Effect of the nature and position of substituents in the aromatic ring on catalytic rearrangement of 1,3-bis(2-chlorophenoxy) and 1,3-bis(4-chlorophenoxy)-2-methylenepropanes
Related Subjects
400201* -- Chemical & Physicochemical Properties
AROMATICS
CARBON TETRACHLORIDE
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHROMATOGRAPHY
CRESOLS
ETHERS
HALOGENATED ALIPHATIC HYDROCARBONS
HOMOGENEOUS CATALYSIS
HYDROGEN TRANSFER
HYDROXY COMPOUNDS
INFRARED SPECTRA
ISOMERIZATION
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHENOLS
SEPARATION PROCESSES
SPECTRA
THERMOCHEMICAL PROCESSES