
TY  - JOUR
A1  - Biffin, MEC 
A1  - Miller, J 
A1  - Moritz, AG 
A1  - Paul, DB 
T1  - Interaction of heterocycles and nucleophiles. II. Sigma complexes formed from methoxide ion and Methoxy-3,5-dinitropyridines in dimethyl sulphoxide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1970
VL  - 23
IS  - 5
SP  - 957
EP  - 962
KW  - 
UR  - https://doi.org/10.1071/CH9700957 
N2  - Contrasting behaviour is observed when 2- and 4-methoxy-3,5-dinitropyridine interact with methoxide ion in dimethyl sulphoxide. The 4-methoxy compound affords both methine and acetal sigma complexes, the latter being thermodynamically more stable. The interconversion is catalysed by methanol. Labelling experiments have established that the sigma complex from the 2-methoxypyridine is formed by addition at C6; no conversion into the acetal could be effected. These observations are rationalized in terms of differential steric and solvation effects. Demethylation and rearrangement reactions of 4-methoxy-3,5-dinitropyridine are reported. 
ER  -

