REAKTIONEN VON PHOSPHOR(III)- TRIMETHYLSILYLESTERN UND ESTERAMIDEN MIT ORTHOCHINONEN; SYNTHESE NEUER 2-TRIMETHYLSILOXYPHENYL-PHOSPHOR- UND PHOSPHINSÄREESTER BZW. -ESTERAMIDE

Abstract

Abstract The reaction of R2POSiMe3 [R [dbnd] Me, Ph, Me2N, O'Pr] with 3,5-di-tert-butyl-o-benzoquinone led to the 2-trimethylsiloxyphenyl phosphoric derivatives 1–4. In the case of the trimethylsilylphosphites (RO)2POSiMe3 [R [dbnd] Me, Et, Ph], the benzo-1,3,2-dioxaphospholines 5–7 were formed by elimination of the corresponding silylethers ROSiMe3. The reaction of R2POSiMe3 [R [dbnd] Me, Me2N, OMe, OiPr, OPh] with tetrachloro-o-benzoquinone produced the 2-trimethylsiloxyphenyl-phosphoric acid esters and esteramides 8–12. The same type of reaction was established between R,POSiMe3 [R [dbnd] Me, Et2N, OMc, OPr, OPh] with 9,10-phenanthrenequinone which produced compounds 13–17. The structure of compound 16 was confirmed by a single crystal X-ray analysis. The reaction of the phosphine oxides R2P(:O)H [R [dbnd] Me, Ph] with 3,5-di-tert-butyl-o-benzoquinone was found to furnish the catechol phosphinic acid esters 18 and 19. The diorganophosphites (RO)2P(:O)H [R [dbnd] Me, OPr, Ph] reacted with tetrachloro-o-...