
%0 Journal Article
%A Pinhey, JT 
%A Xuan, PT 
%T The Thermal <I>ortho</I>-Substitution of Phenols by Vinyl Ethers
%J Australian Journal of Chemistry
%D 1988/01/01
%V 41
%N 1
%P 69-80
%K 
%R https://doi.org/10.1071/CH9880069
%U https://www.publish.csiro.au/paper/CH9880069 
%X 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. 
