THE HYDROCYANATION OF FREE AND POLYMER-BOUND BENZOQUINONE

Article abstract of DOI:10.1016/0040-4020(82)80233-0

The polimer-bound quinone 2 has been prepared and used in column form with organic solvents for the convenient preparation of other quinones.In contrast to the solution reaction hydrocyanation of this quinone by the Thiele-Meisenheimer reaction did not yield a useful proportion of polymer-bound dicyanohydroquinone but instead gave a mixture of products including much monocyanohydroquinone.Helferich and Bodenbender's 2,3-dicyanocyclohexan-1,4-dione is in fact wholly the di-enol and is a likely intermediate in the hydrocyanation of benzoquinone, being oxidised by the latter to 2,3-dicyanocyclohex-2-ene-1,4-dione which tautomerises to the observed product, 2,3-dicyanohydroquinone.A lower accessibility to polymer-bound reactants as compared with those in solution is implied by these results.