Three dimethyltindiamides containing chelating diamide ligands were synthesised from the reaction of the dilithiated diamine and Me2SnCl2; [SnMe2(L1)] 1 (L1 = κ(2)-N(Dipp)C2H4N(Dipp)), [SnMe2(L2)] 2 (L2 = κ(2)-N(Dipp)C3H6N(Dipp)) and [SnMe2(L3)] 3 (L3 = κ(2)-N(Dipp)SiPh2N(Dipp)), Dipp = 2,6-(i)Pr2C6H3. Reaction of (L2)H2 with SnCl4 and NEt3 led to the formation of the diamidotin dichloride [SnCl2(L2)] 4 whereas reaction of (L1)H2 with SnCl4 and NEt3, or [Sn(L1)] with SnCl4, led to the exclusive formation of the amidotin trichloride [SnCl3{κ(2)-DippN(H)C2H4N(Dipp)}] 5. Reactions of [Sn(L1)] with sulfur and selenium formed [{Sn(L1)(μ-E)}2] (E = S 10 and Se )11. MeI reacted with N-heterocyclic stannylenes to generate the Sn(iv) addition products [Sn(Me)I(L1)] 12, [Sn(Me)I(L2)] 13, [Sn(Me)I(L3)] 14 and [Sn(Me)I(L4)] 15 (L4 = κ(3)-N(Dipp)C2H4OC2H4N(Dipp)), and subsequent reaction with AgOTf (OTf = OSO2CF3) generated the corresponding Sn(iv) triflates [Sn(Me)OTf(L1)] 16, [Sn(Me)OTf(L2)] 17 and [Sn(Me)OTf(L4)] 19 with [Sn(Me)OTf(L3)] 18 formed only as a mixture with unidentified by-products. All of the compounds were characterised by single crystal X-ray diffraction.