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

Thermal Sn-C cleavage in the diarylstannylene Sn(Ar iPr4 ) 2 (Ar iPr4 = C 6 H 3 -2,6-(C 6 H 3 -2,6-iPr 2 ) 2 ) was used to generate ˙Sn(Ar iPr4 ) and ˙Ar iPr4 radicals for alkyne arylstannylation. The radical pair and RCCR' (R = H, R' = Ph; R = Ph, R' = Ph; R = H, R' = C 4 H 9 ; R = H, R' = SiMe 3 ) in refluxing benzene generate the aryl vinyl stannylene complexes, Ar iPr4 Sn{C(C 6 H 5 )-C(H)(Ar iPr4 )} (1), Ar iPr4 Sn{C(C 6 H 5 )-C(H)(C 6 H 5 )} (2) and Ar iPr4 Sn{C(C 4 H 9 )-C(H)(Ar iPr4 )} (3) respectively. For HCCSiMe 3 , the known distannene {Sn(CCSiMe 3 )Ar iPr4 } 2 (4) was also generated from this new method.