96107-88-9Relevant academic research and scientific papers
Positional Selectivity of the Methylation of 5-Substituted Tetrazolate Anions
Spear, Robert J.
, p. 2453 - 2468 (2007/10/02)
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 electronegativity and steric bulk lead to predominant methylation at N 2.Sodium 5-ethoxycarbonyltetrazolate (3n) goes against this trend and an intermediate is proposed where the incoming electrophile is associated with the ester carbonyl group.
