The chemistry of pentavalent organobismuth reagents. Part 8. Phenylation and oxidation of alcohols by tetraphenylbismuth esters
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 251-259
- https://doi.org/10.1039/p19870000251
Abstract
Tetraphenylbismuth trifluoroacetate under neutral or slightly acidic conditions O-phenylates primary alcohols in reasonable (65–75%) 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 BiV reagents with alcohols under basic conditions gives, exclusively, oxidation, often with benzene as a leaving group. The presence of a BiV intermediate with a bismuth–oxygen bond has been proved in several different ways using n.m.r. spectroscopy. Thus the reactions of alcohols with BiV reagents parallel the corresponding reactions with phenols.Keywords
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