108529-97-1Relevant academic research and scientific papers
The Catalytic Effect of Copper Ions in the Phenylation Reaction of David and Thieffry
Barton, Derek H. R.,Finet, Jean-Pierre,Pichon, Clotilde
, p. 65 - 66 (1986)
Several types of bifunctional molecules are smoothly phenylated by triphenylbismuth diacetate in a reaction which has an induction period, a curious solvent dependence, and the need for illumination; however, the addition of a small amount of Cu(OAc)2 removes all these limitations and accelerates greatly the reaction.
The Chemistry of Pentavalent Organobismuth Reagents. Part 8. Phenylation and Oxidation of Alcohols by Tetraphenylbismuth Esters
Barton, Derek H. R.,Finet, Jean-Pierre,Motherwell, William B.,Pichon, Clotilde
, p. 251 - 260 (2007/10/02)
Tetraphenylbismuth trifluoroacetate under neutral or slightly acidic conditions O-phenylates primary alcohols in reasonable (65-75percent) yield, but gives only moderate yields with secondary alcohols and no O-phenylation with tertiary alcohols.An SN2 type mechanism is proposed with attack of oxygen on aryl carbon.In contrast, the reaction of Bi(V) reagents with alcohols under basic conditions gives, exclusively, oxidation, often with benzene as a leaving group.The presence of a Bi(V) intermediate with a bismuth-oxygen bond has been proved in several different ways using n.m.r. spectroscopy.Thus the reactions of alcohols with Bi(V) reagents parallel the corresponding reactions with phenols.
