An isolable stannaimine and its cycloaddition/metathesis reactions with carbon dioxide

Matthew J Evans; Joseph M Parr; Dat T Nguyen; Cameron Jones

doi:10.1039/d4cc04006f

An isolable stannaimine and its cycloaddition/metathesis reactions with carbon dioxide

Chem Commun (Camb). 2024 Sep 16;60(75):10350-10353. doi: 10.1039/d4cc04006f.

Authors

Matthew J Evans¹, Joseph M Parr¹, Dat T Nguyen¹, Cameron Jones¹

Affiliation

¹ School of Chemistry, Monash University, Melbourne, PO Box 23, Victoria, 3800, Australia. [email protected].

PMID: 39219473
DOI: 10.1039/d4cc04006f

Abstract

An N-heterocyclic stannylene :Sn(NON^Ad) (NON^Ad = [O(SiMe₂NAd)₂]^2-, Ad = 1-adamantyl), reacts rapidly with 2,4,6-tricyclohexylphenyl azide (TCHP)N₃, affording a stannaimine, (NON^Ad)SnN(TCHP). Solutions of (NON^Ad)SnN(TCHP) react immediately with carbon dioxide (CO₂) to give a [2+2]-cycloaddition product, which, upon heating, subsequently engages in a metathesis process to give [Sn(NON^Ad)(μ-O)]₂ and the bulky isocyanate, (TCHP)NCO.