
TY  - JOUR
A1  - Brown, DJ 
A1  - Lee, T 
T1  - Pyrimidine reactions. XVI. Thermal rearrangement of substituted 2- and 4-alkoxypyrimidines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1968
VL  - 21
IS  - 1
SP  - 243
EP  - 255
KW  - 
UR  - https://doi.org/10.1071/CH9680243 
N2  - Thermal rearrangement of methyl, bromo, and nitro derivatives of 2- and 4-alkoxy-pyrimidines produced their N-alkyl isomers. These were identified by p.m.r. spectral comparison with synthetic specimens of unambiguous or proven structure. The rates for such isomerizations were measured conveniently by changes in ultraviolet spectra. The C-methyl derivatives rearranged more slowly than the parent alkoxypyrimidines, but the bromo, and especially the nitro, derivatives did so much more quickly. Among the derivatives of each methoxy-pyrimidine, the rate of rearrangement increased as the basic pKa value fell and as the methoxyl protons moved downfield, thus affording a qualitative correlation with properties reflecting the electronic effect of each substituent. 
ER  -

