
TY  - JOUR
A1  - Spear, RJ 
T1  - Positional selectivity of the methylation of 5-substituted tetrazolate anions
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1984
VL  - 37
IS  - 12
SP  - 2453
EP  - 2468
KW  - 
UR  - https://doi.org/10.1071/CH9842453 
N2  - The methylation of a series of 15 sodium 5-substituted tetrazolates using iodomethane in acetone/water (4 : 1) has been studied. The reaction yields both 1- and 2-methyl products, and the ratio of these products is discussed in terms of the nature of the 5-substituent. Electronic and steric effects dominate the reaction pathway; both increased substituent electro negativity and steric bulk lead to predominant methylation at N2. Sodium 5-ethoxycarbonyltetrazolate (3n) goes against this trend and an intermediate is proposed where the incoming electrophile is associated with the ester carbonyl group. 
ER  -

