Reaction of o-benzoquinones with benzylidenetriphenylphosphorane under the conditions of the common effect of high pressure and shear deformation

Abstract

When the isomeric 3,5- and 3,6-di-tert-butyl-o-benzoquinones are reacted with benzylidenetriphenylphosphorane under the combined effect of high pressure and shear deformation the benzylidene ethers of the corresponding pyrocatechol are formed, in contrast to the analogous reactions of the indicated o-quinones in a two-phase catalytic system at atmospheric pressure. The observed change in the composition of the transformation products is related to a change in the electron distribution of the C-P bond of the ylide under the effect of HP+SD.