
TY  - JOUR
A1  - Pinhey, JT 
A1  - Xuan, PT 
T1  - The Thermal <I>ortho</I>-Substitution of Phenols by Vinyl Ethers
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1988
VL  - 41
IS  - 1
SP  - 69
EP  - 80
KW  - 
UR  - https://doi.org/10.1071/CH9880069 
N2  - Pyrolysis of a mixture of phenol and 3,4-dihydro-2H-pyran (6) at 150- 180&#176;C resulted in the formation of 2-(tetrahydro-2H-pyran-2-yl)phenol (3a) in moderate yield. This selective ortho-substitution reaction has been investigated for a range of phenols and a number of vinyl ethers. While it was found to be a fairly general reaction for phenols, only with the vinyl ether (6) and 2,3-dihydrofuran (28a) was the reaction found to be regioselective. Aluminium phenylate strongly catalyses the reaction of phenol with (6), which proceeded under these conditions at room temperature. An ene -type mechanism is proposed for the reaction. 
ER  -

