Ring-fused hexahydro-1,2,4,5-tetrazines: synthesis, structure, and mechanistic studies on isolable rotational isomers

Yasunori Toda; Airi Kooguchi; Kimiya Sukegawa; Ayaka Kikuchi; Hiroyuki Suga

doi:10.1039/d2cc06170h

Ring-fused hexahydro-1,2,4,5-tetrazines: synthesis, structure, and mechanistic studies on isolable rotational isomers

Chem Commun (Camb). 2023 Jan 17;59(6):700-703. doi: 10.1039/d2cc06170h.

Authors

Yasunori Toda¹, Airi Kooguchi¹, Kimiya Sukegawa¹, Ayaka Kikuchi¹, Hiroyuki Suga¹

Affiliation

¹ Department of Materials Chemistry, Faculty of Engineering, Shinshu University, 4-17-1, Wakasato, Nagano, 380-8553, Japan.

PMID: 36537160
DOI: 10.1039/d2cc06170h

Abstract

We designed conformationally stable rotational isomers around the C(sp²)-C(sp³) axis at the C₃-position of hexahydro-1,2,4,5-tetrazines. Isolation of each rotamer by silica gel column chromatography was successfully achieved at room temperature. The proposed isomerization mechanism of the rotamers was supported by NMR kinetic studies.