THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS. PART XI. REACTIONS WITH STERICALLY HINDERED PHENOLS.
The reactivity of BiV reagents towards very hindered phenols with tert.-butyl groups at 2 and 6 under basic conditions has been studied.Unexpected phenylation at the 4-position and, in several cases, replacement of a tert.-butyl group by phenyl have been observed.The mechanism of these unexpected reactions has been discussed.
Barton, Derek H. R.,Finet, Jean-Pierre,Gianotti, Charles,Halley, Frank
p. 4483 - 4494
(2007/10/02)
THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS. PART X. STUDIES ON THE PHENYLATION AND OXIDATION OF PHENOLS
The influence of the substituents on the phenol on the regiochemistry of the arylation reactions with Ph3BiCl2 and other bismuth reagents has been studied.O-Phenylation occurs with phenols substituted with electron-withdrawing groups.Electron-donating substituted phenols undergo ortho C-phenylation.Oxidative dimerisation has been observed with 2,6-dialkyl phenols.
Barton, Derek H. R.,Yadav-Bhatnagar, Neerja,Finet, Jean-Pierre,Khamsi, Jamal,Motherwell, William B.,Stanforth, Stephen P.
p. 323 - 332
(2007/10/02)
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