1190-78-9Relevant articles and documents
Reaction of 1-alkenyl and 1-alkynyl derivatives of tin and mercury with hetero-centered radicals
Russell, Glen A.,Ngoviwatchai, Preecha,Tashtoush, Hasan,Hershberger, James
, p. 1414 - 1419 (2008/10/08)
1-Alkenyl and 1-alkynyl derivatives of tin and mercury react with hetero-centered radicals such as RS., PhSe., PhSO2., or (EtO)2P(O). to undergo substitution of the metal atom in a free radical chain reaction involving addition-elimination. The hetero-centered radical can be formed in a chain propagation reaction by the attack of ClHg. or Bu3Sn. upon reagents such as RSSR, PhSeSO2Ph, PhSeSePh, or PhSO2Cl or mercurials such as Hg(SPh)2, Hg(SePh)2, Hg(O2SPh)2, or Hg[(O)P(OEt)2]2. In relative reactivity studies toward PhS., vinylmercury chlorides are somewhat more reactive than the analogous tri-n-butylstannanes. Tri-n-butyl(phenylethynyl)stannane is 300 times less reactive than its β-styrenyl analogue. Toward PhS., CH2=CHCH2SnBu3 is 3 times as reactive as CH2=CHSnBu3 but only 1/16 as reactive as (E)-PhCH= CHSnBu3. An explanation is advanced for the observations that PhSeSePh participates in a free radical chain substitution reaction with allylstannanes or 1-alkenylmercury chlorides but not with 1-alkenylstannanes although PhSSPh or (PhSe)2Hg react readily with 1-alkenylmercurials or -stannanes.
