Methylrhenium trioxide, also known as methyltrioxorhenium(VII), is an organometallic compound with the formula CH3−ReO3. It is a volatile, colourless solid that has been used as a catalyst in some laboratory experiments. This chemical substance adopts a tetrahedral molecular geometry with rhenium surrounded by one methyl and three oxo ligands. The oxidation state of rhenium is +7.

Synthesis

Methylrhenium trioxide is commercially available. It can be prepared by many routes, a typical method is the reaction of rhenium heptoxide and tetramethyltin:[1]

Re2O7 + (CH3)4Sn → CH3ReO3 + (CH3)3Sn−O−ReO3

Analogous alkyl and aryl derivatives are known. Compounds of the type R−ReO3 are Lewis acids, forming both 1:1 and 1:2 adducts with halides and amines.

Uses

Methylrhenium trioxide serves as a heterogeneous catalyst for a variety of transformations. Supported on alumina/silica, it catalyzes olefin metathesis at 25 °C.

In solution, methylrhenium trioxide catalyses for the oxidations with hydrogen peroxide. Terminal alkynes yield the corresponding carboxylic acid or ester, internal alkynes yield diketones, and alkenes give epoxides. Methylrhenium trioxide also catalyses the conversion of aldehydes and diazoalkanes into an alkene,[2] and the oxidation of amines to N-oxides with sodium percarbonate.[3]

References

  1. ^ Herrmann, W. A.; Kratzer R. M.; Fischer R. W. (1997). "Alkylrhenium Oxides from Perrhenates: A New, Economical Access to Organometallic Oxide Catalysts". Angew. Chem. Int. Ed. Engl. 36 (23): 2652–2654. doi:10.1002/anie.199726521.
  2. ^ Hudson, Andrew; Betz, Daniel; Kühn, Fritz E.; Jiménez-Alemán, Guillermo H.; Boland, Wilhelm (2013-09-16). "Methyltrioxorhenium". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289x.rn00017.pub3. ISBN 978-0-471-93623-7.
  3. ^ Jain, Suman L.; Joseph, Jomy K.; Sain, Bir (2006). "Rhenium-Catalyzed Highly Efficient Oxidations of Tertiary Nitrogen Compounds to N-Oxides Using Sodium Percarbonate as Oxygen Source". Synlett (16): 2661–2663. doi:10.1055/s-2006-951487.
Allikas: http://en.wikipedia.org/wiki/Methyltrioxorhenium
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