The N‐heterocyclic stannylenes [{Fe(η$^5$‐C$_5$H$_4$‐NSi𝑡 BuMe$_2$)$_2$}Sn] (1 ) and [𝘰‐C$_6$H$_4$(NSi𝑡 BuMe$_2$)]$_2$Sn (2 ) were prepared in one‐pot reactions from SnCl$_2$, LiN(SiMe$_3$)$_2$, and the corresponding diamine, viz. [Fe(η$^5$‐C$_5$H$_4$‐NHSi𝑡 BuMe$_2$)$_2$] and 𝘰‐C$_6$H$_4$(NSiH𝘵 BuMe$_2$)$_2$, respectively. Oxidative addition reactions of 1 and 2 with S$_8$ and Se$_8$, respectively, afforded the corresponding 1,3,2,4‐dithiadistannetanes ((1 S$_2$), (2 S$_2$)), and 1,3,2,4‐diselenadistannetanes [(1 Se)$_2$, (2 Se)$_2$]. The reactions of 1 and 2 with PhSeSePh respectively furnished 1 (SePh)$_2$ and 2 (SePh)$_2$. The crystal structures of 𝘰‐C$_6$H$_4$(NSiH𝑡 BuMe$_2$)$_2$, 1, 2, ( 1 S)$_2$, (2 S)$_2$, (1 Se)$_2$, (2 Se)$_2$, 1 (SePh)$_2$, and 2 (SePh)$_2$ were determined by single‐crystal X‐ray diffraction. Stannylene 2 shows a chain‐like aggregation in the solid state due to intermolecular Sn⋯arene interactions. A short intramolecular CH⋯Se contact compatible with a hydrogen bond was observed for (1 Se)$_2$.