42995-54-0Relevant academic research and scientific papers
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.
