"Super stable" Blatter radicals through ArLi addition: surprising chemistry of 7-(trifluoromethyl)benzo[ e][1,2,4]triazine

Emilia Obijalska; Anna Pietrzak; Christos P Constantinides; Roger D Sommer; Piotr Kaszyński

doi:10.1039/d3cc00832k

"Super stable" Blatter radicals through ArLi addition: surprising chemistry of 7-(trifluoromethyl)benzo[ e][1,2,4]triazine

Chem Commun (Camb). 2023 Mar 30;59(27):4008-4011. doi: 10.1039/d3cc00832k.

Authors

Emilia Obijalska¹, Anna Pietrzak², Christos P Constantinides³, Roger D Sommer³, Piotr Kaszyński^{1

4

5}

Affiliations

¹ Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland. piotr.kaszynski@chemia.uni.lodz.pl.
² Faculty of Chemistry, Łódź University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
³ Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.
⁴ Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Łódź, Poland.
⁵ Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37130, USA.

PMID: 36916722
DOI: 10.1039/d3cc00832k

Abstract

Addition of PhLi to 7-(CF₃)benzo[e][1,2,4]triazine at -78 °C gives the "super stable" Blatter radical in high yields, while above -5 °C two additional products are formed. XRD analysis revealed the formation of a "trimer" and a benzo[f][1,2,4]triazepine via a novel mechanism. The latter is formed from the anion generated from the isolated radical, which suggests its instability in organic batteries.