C(3) Functional Derivatives of the Blatter Radical

Abstract

A series of 3-substituted 1-phenyl-1,4-dihydrobenzo[<i>e</i>][1,2,4]triazin-4-yls <b>1</b> was prepared by addition of PhLi to 3-substituted benzo[<i>e</i>][1,2,4]triazines <b>2</b> followed by aerial oxidation. The scope of the C(3) substituents in the reaction was investigated, and 10 structurally diverse radicals <b>1</b> were isolated, their stability was assessed and properties were investigated with spectroscopic and electrochemical methods. Two radicals were analyzed with single-crystal XRD methods. Experimental data are compared to DFT results and correlated with Hammett substituent parameters.