
TY  - JOUR
A1  - Lister, Troy 
A1  - Prager, Rolf H. 
A1  - Tsaconas, Michael 
A1  - Wilkinson, Kerry L. 
T1  - On the Thermally Induced Rearrangement of 2-Alkoxypyridines to <emph type="2">N</emph>-alkylpyridones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2003
VL  - 56
IS  - 9
SP  - 913
EP  - 916
KW  - 
UR  - https://doi.org/10.1071/CH03044 
N2  - 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. 
ER  -

