113303-15-4Relevant articles and documents
Substitution Reactions in the β-Styryl and Phenylethynyl Systems
Russell, Glen A.,Ngoviwatchai, Preecha
, p. 1836 - 1842 (2007/10/02)
Substitution for Q in the systems PhCH=CHQ, Ph2C=CHQ, and PhCCQ can occur by a free-radical chain mechanism where the attacking radical is alkyl (Q = HgX, Bu3Sn, PhSO2, PhSO, PhS, Cl, Br, I) or (EtO)2PO. (Q = HgX, Bu3Sn, I).The Q. radicals formed by β-elimination can generate t-Bu. or (EtO)2PO. by reaction with t-BuHgCl, Hg2, ClHg or by electron transfer between .HgCl and (EtO)2PO-.With Q = PhS or PhSO2, relative reactivity data indicates that the free radical addition-elimination sequence occurs for t-BuLi at 0 or 45 deg C andthat this process may also be involved in reactions of t-BuMgCl or tert-butyl cuprates with some of the substrates.Ionic reaction of (EtO)2PO- with the three substrates with Q = PhSO2 or halogen are examined.With Q = PhSO2, PhCHCH2P(O)(OEt)2, Ph2C=CHP(O)(OEt)2, and PhCCP(O)(OEt)2 are formed in good yield.