
%0 Journal Article
%A Lister, Troy 
%A Prager, Rolf H. 
%A Tsaconas, Michael 
%A Wilkinson, Kerry L. 
%T On the Thermally Induced Rearrangement of 2-Alkoxypyridines to <emph type="2">N</emph>-alkylpyridones
%J Australian Journal of Chemistry
%D 2003/08/08
%V 56
%N 9
%P 913-916
%K 
%R https://doi.org/10.1071/CH03044
%U https://www.publish.csiro.au/paper/CH03044 
%X Analogues of 2-methoxypyridine undergo rearrangement to N-methylpyridones under flash vacuum pyrolysis (FVP) conditions. Ethoxy derivatives undergo competitive ethyl migration and elimination of ethylene. Analogues of 4-methoxypyridine do not undergo rearrangement under FVP conditions, but demethylation on silica may occur. The ease of rearrangement follows the basicity of the alkoxyhetarene to some extent. The vapour-phase rearrangements have been contrasted to condensed-phase pyrolyses, and a four-centre transition state for the former is supported by computation. The rearrangement allows structural assignment to the two products from the reaction of 2,4-dichloroquinoline with pyrrolidine. 
