Synthesis, structure and N–N bonding character of 1, 1-disubstituted indazolium hexafluorophosphate. Issue 15 (2nd February 2018)

• Record Type: Journal Article
• Authors: Ning, Yingtang; Kawahata, Masatoshi; Yamaguchi, Kentaro; Otani, Yuko; Ohwada, Tomohiko
• Is Part Of: Chemical communications. Volume 54:Issue 15(2018)
• Page Start: 1881
• Page End: 1884
• Publication Date: 2018-02-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc00183a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An efficient method for the synthesis of thermodynamically unstable 1, 1-disubstituted indazolium by means of intramolecular electrophilic amination under mild conditions was reported. Abstract : 1, 1-Disubstituted indazolium hexafluorophosphates were synthesized via intramolecular electrophilic amination reactions under mild conditions. The crystal structures were determined and are consistent with the presence of a stable N–N bond, which can be cleaved by hydrogenation. Both experimental and computational studies suggest a covalent bonding character of the N–N bond, with diminished aromaticity of the newly formed pyrazolium ring due to the quaternary ammonium atom (N1), in contrast to the aromatic character of the parent indazole.