Silylation–desilylation of quinones and their derivatives

Abstract

The silylation of quinones and their substituted derivatives for the protection of the reactive quinonic moiety and/or reactive substituents (in particular hydroxyl groups) is discussed in view of the wide applicability of the reaction for synthetic, biological and analytical purposes. Furthermore, the most common and efficient methods for the subsequent desilylation of the silylated quinones and their derivatives to the parent quinones or to the corresponding hydroquinones are discussed.

Recent advances in 1,4-benzoquinone chemistry

“…13 Wide applications of quinones can also be found in the field of synthetic organic chemistry. [14][15][16][17][18][19][20] Coordination chemistry of quinones is also quite rich from the perspective of designing magnetic materials 21 and understanding photophysical properties. 22 The studies of quinonoid compounds have focused on a broad spectrum of topics viz occurrence in nature, 2 syntheses, 23 cycloaddition reactions, 24 photochemistry and pulse radiolysis, 1,25,26 computational chemistry, etc.…”

“…El-Feraly and co-workers 52 isolated five new alkylated benzoquinones (16)(17)(18)(19)(20) as methyl ether derivatives from a complex mixture of alkylated hydroxy benzoquinones obtained from the fruits of Maesa lanceolata.…”

Review: Synthetic methodologies in siloxanes

“…51 (1) Co-hydrolysis of trifunctional organo-or hydro-silanes. For example cohydrolysis of HSiCl 3 Silsesquioxane also have three subclasses; they are (1) functional silsesquioxanes, (2) nonfunctional silsesquioxanes and (3) bridged polysilsesquioxanes.…”

“…A porous solid derived from a siloxane [Si-O] n network 57 having an imino bis(N-2-aminoethylacetamide) polysiloxane ligand system has been found to be very effective for the uptake of metal ions such as Mn 2+ , Fe 3+ , Co 2+ , Ni 2+ , Cu 2+ and Zn 2+ . An iodo-functionalized modified siloxane network 58 ([Si-O] n ) has recently been prepared by polycondensation of Si(OEt) 4 and (MeO) 3 Si(CH 2 ) 3 I. This siloxane network exhibits high uptake of various di-and tri-valent cations.…”

“…60 Bilayer within bilayers 61 of silahydroxy compounds can provide nanodimensional confinements. Si-C bond formation reactions are achieved at the porous silicon surfaces by immobilization 62 of RhCl(PPh 3 ) 3 . In a more recent report, gold nanoparticles are used as catalysts for polymerization of alkylsilane to obtain nanowires, filaments and tubes.…”