Trimethylsilyl-Induced N-O Bond Cleavage in Nitrous Oxide-Derived Aminodiazotates

Yizhu Liu; Léonard Y M Eymann; Euro Solari; Farzaneh Fadaei Tirani; Rosario Scopelliti; Kay Severin

doi:10.1021/acs.inorgchem.8b02129

Trimethylsilyl-Induced N-O Bond Cleavage in Nitrous Oxide-Derived Aminodiazotates

Inorg Chem. 2018 Oct 1;57(19):11859-11863. doi: 10.1021/acs.inorgchem.8b02129. Epub 2018 Sep 14.

Authors

Yizhu Liu¹, Léonard Y M Eymann¹, Euro Solari¹, Farzaneh Fadaei Tirani¹, Rosario Scopelliti¹, Kay Severin¹

Affiliation

¹ Institut des Sciences et Ingénierie Chimiques , École Polytechnique Fédérale de Lausanne (EPFL) , CH-1015 Lausanne , Switzerland.

PMID: 30215513
DOI: 10.1021/acs.inorgchem.8b02129

Abstract

The chemical activation of nitrous oxide (N₂O) typically results in O-atom transfer and the extrusion of N₂ gas. In contrast, reactions of N-trimethylsilyl (TMS)-substituted amides with N₂O give inorganic or organic azides, with concomitant formation of silanols or siloxanes. N-TMS-substituted amides are also able to induce N-O bond cleavage in N₂O-derived dialkylaminodiazotates, generating tetrazene salts. These results indicate the potential of silyl groups in devising transformations, in which N₂O acts as an N-atom donor.