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VO (OR) Cl2 is revealed to be a Lewis acid with one-electron oxidation capability. The regioselective ringopening oxygenation of cyclic ketones is catalyzed by VO (OEt) Cl2 in ethanol under oxygen to give the diesters or keto esters. The presence of α, β carbon-carbon double bond in the ketones alters the reaction course. 2-Cyclohexen-l-ones undergo dehydrogenative aromatization to give aryl ethers. An oxovanadium compound obtained from VO (OEt) Cl2 and AgOTf or Me3SiOTf works more efficiently. In the cases of 2-cyclopenten-1- ones, 1-acetyl-1-cyclohexene, and β-ionone, allylic oxidation is achieved to introduce an oxo or alkoxyl group at the γ-position. 2-Phenylglycine derivatives are transformed to ethyl benzoate and ethyl phenylglyoxylate by the VO (OEt) Cl2-induced' oxidative deamination and/or decarboxylation. The ring-opening addition of cyclobutanone to olefins bearing an electron-withdrawing group leads to the corresponding E-chloro ester via oxidation of a cyclobutoxide intermediate. Treatment of a mixture of diketene and styrenes with VO (OR) Cl2 gives 3-alkoxycarbony1-2-methyl-5-phenyl-4, 5-dihydrofurans.Oxidative desilylation is selectively realized by one-electron oxidation of organosilicon compounds with VO (OEt) Cl2. Silyl enol ethers undergo the oxidative cross coupling to afford unsymmetrical 1, 4-diketones. Allylic silanes also regioselectively dimerize to 1, 5-hexadienes. Oxidative desilylation of silyl enol ethers and allylic silanes selectively gives γ, δ-unsaturated ketones depending on their redox potentials.The highly stereoselective monodebromination of gem-dibromocyclopropanes is induced or catalyzed by a low valent vanadium species generated from vanadium (III) chloride or CpV (CO) 4 and zinc in dimethoxyethane in a combination with diethyl phosphonate or triethyl phosphite.

Synthetic Reactions via Vanadium-Induced One-Electron Redox.