Sn(II)-carbon bond reactivity: radical generation and consumption reactions of a stannylene with alkynes.

Thermal Sn-C cleavage in the diarylstannylene Sn(Ar) (Ar = CH-2,6-(CH-2,6-iPr)) was used to generate ˙Sn(Ar) and ˙Ar radicals for alkyne arylstannylation. The radical pair and RCCR' (R = H, R' = Ph; R = Ph, R' = Ph; R = H, R' = CH; R = H, R' = SiMe) in refluxing benzene generate the aryl vinyl stannylene complexes, ArSn{C(CH)-C(H)(Ar)} (1), ArSn{C(CH)-C(H)(CH)} (2) and ArSn{C(CH)-C(H)(Ar)} (3) respectively. For HCCSiMe, the known distannene {Sn(CCSiMe)Ar} (4) was also generated from this new method.