Vanadyl acetylacetonate

Vanadyl(acetylacetonate) is the chemical compound with the formula VO(C₅H₇O₂)₂. This blue-green coordination complex consists of the vanadyl group, VO²⁺, bound to two acetylacetonate anions, acac⁻. Like other charge-neutral acetylacetonates, this complex is soluble in organic solvents.

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Synthesis

The complex is prepared from vanadium(IV) or vanadium(V) precursors, the latter being more convenient:^[1]

2 V₂O₅ + 9 C₅H₈O₂ → 4 VO(C₅H₇O₂)₂ + (CH₃CO)₂O + 5 H₂O

Structure and properties

The complex has a square pyramidal structure with a short V=O bond. This d¹ compound is paramagnetic. Its optical spectrum exhibits two transtions. It is a weak Lewis acid, forming adducts with pyridine and methylamine.^[1]

Applications

It is used in organic chemistry as a reagent in the epoxidation of allylic alcohols in combination with tert-butylhydroperoxide (TBHP). The VO(acac)₂-TBHP system is exclusively epoxidizes geraniol at the allylic alcohol position. For comparison, another epoxidizing agent m-CPBA, reacts exclusively with the other alkene group. TBHP oxidizes VO(acac)₂ to a vanadium(V) species which coordinates the alcohol of the substrate and the hydroperoxide.^[2]