Isolation of the quinone mono O,S-acetal intermediates of the aromatic pummerer-type rearrangement of p-sulfinylphenols with 1-ethoxyvinyl esters

Article abstract of DOI:10.1002/anie.199715291

A versatile synthetic building block and evidence for the mechanism of the Pummerer-type rearrangement have been obtained in the form of the acetal intermediate B, isolated in the reaction of p-sulfinylphenols 1 to p-quinones 2 induced by acid anhydrides. Thus, a method is now also available for the efficient preparation of quinone monoacetals under nonoxidative conditions.