Organophosphorus compounds—XIX : The reaction of trialkyl phosphites with extended p-quinones

Abstract

Trimethyl and triethyl phosphites react with diphenoquinone 3, yielding 4,4′-dihydroxydiphenyl 10; 4′-alkoxy-4-biphenylyl dialkyl phosphates 5, 4,4′-biphenylylene tetraalkyl bis(phosphates), 6, and 4′-hydroxy-4-biphenylyl dialkyl phosphates 9 are also isolated in minor yields. The effect of temperature on the reaction is studied. A mechanism for the reaction is presented which accounts for the experimental results. The reaction of trimethyl and triethyl phosphites with quinoneimines 12 gives the corresponding phosphoramidates 13, in quantitative yields.