2189-88-0Relevant academic research and scientific papers
Neopentylation of Phenols and Hydroquinones
Quast, Helmut,Schulze, Johannes
, p. 509 - 512 (2007/10/02)
Neopentylation of phenol, the hydroquinones 6 as well as the hydroquinone diacetates 8 by means of neopentyl iodide in diethylene glycol dimethyl ether in the presence of cesium carbonate affords high yields of the neopentyl ethers 2a and 7, respectively.
PREPARATION OF ALKYL-ARYL ETHERS AND THIOETHERS
Downie, Ian M.,Heaney, Harry,Kemp, Graham
, p. 2619 - 2624 (2007/10/02)
A method, which involves no molecular rearrangement, and which is also stereospecific, for the preparation of alkyl-aryl ethers and thioethers is described.Stable alkoxyphosphonium salts, R-O-P(1+)(NMe2)3 PF6(1-), have been prepared and treated with phenols and thiophenols, under basic conditions, to yield the corresponding alkyl-aryl ethers and thioethers respectively.
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.
