REDUCTIVE SILYLATION OF QUINONES CATALYZED BY TRIS(TRIPHENYLPHOSPHINE)CHLORORHODIUM(I) - OXIDATIVE DESILYLATION

Tris(triphenylphosphine)chlororhodium(I) has been found to be an effective catalyst for the homogeneous reductive silylation of quinones with triethylsilane. The reactions offer an easy procedure for protecting the highly reactive quinonic groups of naturally occurring and biologically important macromolecules. The bis(silyl) ethers of the hydroquinone derivatives are found to readily undergo oxidative desilylation upon their reaction with (diacetoxyiodo)benzene. Finally, all silyl ethers produced undergo acid hyorolysis to give the corresponding hydroquinone derivatives.