biostudies-literatureFischer MLeverhulme TrustAlexander von Humboldt-StiftungEngineering and Physical Sciences Research Councile202211616https://www.ebi.ac.uk/biostudies/studies/S-EPMC9828258biostudies-literatureUnknown61(48)A systematic study to access stable stannaimines is reported, by combining different heteroleptic stannylenes with a range of organic azides. The reactions of terphenyl-/hypersilyl-substituted stannylenes yield the putative tin nitrogen double bond, but is directly followed by 1,2-silyl migration to give Sn^II systems featuring bulky silylamido ligands. By contrast, the transition from a two σ donor ligand set to a mixed σ-donor/π-donor scaffold allows access to three new stannaimines which can be handled at room temperature. The reactivity profile of these Sn=N bonded species is crucially dependent on the substituent at the nitrogen atom. As such, the Sn=NMes (Mes=2,4,6-Me₃ C₆ H₂ ) system is capable of activating a broad range of substrates underAngewandte Chemie (International ed. in English)Taming Heavier Group 14 Imine Analogues: Accessing Tin Nitrogen [Sn=N] Double Bonds and their Cycloaddition/Metathesis Chemistry.PMC9828258RP-2018-246EP/S023828/1Roy MMDEllwanger MAMcManus CWales LLRoper AFFischer MHeilmann AAldridge SfalseTaming Heavier Group 14 Imine Analogues: Accessing Tin Nitrogen [Sn=N] Double Bonds and their Cycloaddition/Metathesis Chemistry.A systematic study to access stable stannaimines is reported, by combining different heteroleptic stannylenes with a range of organic azides. The reactions of terphenyl-/hypersilyl-substituted stannylenes yield the putative tin nitrogen double bond, but is directly followed by 1,2-silyl migration to give Sn^II systems featuring bulky silylamido ligands. By contrast, the transition from a two σ donor ligand set to a mixed σ-donor/π-donor scaffold allows access to three new stannaimines which can be handled at room temperature. The reactivity profile of these Sn=N bonded species is crucially dependent on the substituent at the nitrogen atom. As such, the Sn=NMes (Mes=2,4,6-Me₃ C₆ H₂ ) system is capable of activating a broad range of substrates under2022-01-01T00:00:00Z2022 Nov2026-03-27T15:40:17.691Z2025-04-05T10:26:31.039ZS-EPMC98282583616174910.1002/anie.202211616