SELF-ASSOCIATION OF TRIMETHYLSILYL-3,6-DI-tert-BUTYL-o-SEMIQUINONE

Article abstract of DOI:10.1007/BF00863825

The reaction of sodium 3,6-di-tert-butyl-o-semiquinolate with Me3SiCl in THF leads to the formation of 2-(2'-trimethylsiloxy-3',6'-di-tert-butylphenoxy)-2-trimethylsiloxy-3,6-di-tert-butylcyclohexadien-3,5-one 1.On the basis of IR and UV spectroscopy and analysis of the reaction products, it has been determined that the cyclohexadiene structure 1 is preserved on heating to moderate temperatures or on reaction with water or HCl, but photolysis leads to its decomposition, and so does reaction with metallic sodium or alkali.A scheme of the process is propounded.Keywords: di-tert-butyl-substituted oxyphenoxyl radicals, self-associates, trimethylsilyl-o-semiquinone, cyclohexadiene structures, geminal recombination reactions.