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Methyltrioxorhenium(VII) is used as a catalyst for various transformations such as olefin metathesis. It is associated with hydrogen peroxide and used as an oxidizing agent. It is used to prepare acid or ester from the corresponding terminalalkynes. It is a catalytic oxidant used with urea hydrogen peroxide to prepare nitrones. It reacts with 2-methylnaphthalene to get 2-methyl-1,4-naphthoquinone (Vitamin K3). Further, it catalyzes the reaction with aldehydes and diazoketones to get an alkene. In addition to this, it is used as an effective antioxidant under various conditions.
Useful catalyst, soluble in organic solvents and water, and stable to air and acids: J. Organomet. Chem., 372, 351 (1989). Investigated by Herrmann's group as an alkene metathesis catalyst: Angew. Chem. Int. Ed., 30, 1636 (1991), a catalyst for clean epoxidation of alkenes with H2O2: Angew. Chem. Int. Ed., 30, 1638 (1991), and to promote the olefination of aldehydes with diazo esters: Angew. Chem. Int. Ed., 30, 1641 (1991). The activation of H2O2 in epoxidation and other reactions has been extensively studied; feature article: Chem. Commun., 479 (1999). Improved results in epoxidations with H2O2 in the presence of pyrazole have been reported by Herrmann: J. Organomet. Chem., 555, 293 (1998), and by Sharpless with pyrazole, pyridine or 3-cyanopyridine: Tetrahedron Lett., 40, 3991 (1999); J. Org. Chem., 65, 8651 (2000); see also Tetrahedron Lett., 39, 8521 (1998). For use in the Baeyer-Villiger oxidation of ketones, see: Angew. Chem. Int. Ed., 37, 1198 (1998); the reaction can also be carried out with H2O2 in ionic liquids at room temperature: Tetrahedron Lett., 44, 8991 (2003). Catalyzes the oxidative cleavage of ɑ-hydroxy carbonyl compounds to carboxylic acids with H2O2: Synth. Commun., 33, 3875 (2003). High yield aerobic oxidation of various organonitrogen compounds has been described: e.g. pyridines to N-oxides, anilines to nitrobenzenes and sec-amines to nitrones: Tetrahedron Lett., 44, 3235 (2003).
For a brief feature on uses in synthesis, see: Synlett, 1849 (2004).
Hou, J.; Chen, Y.; Ma, D.; Cordes, B.; Wang, J.; Wang, X.; Kühn, F. E.; Guo, H.; Zhou, M. Methyltrioxorhenium-catalyzed highly selective dihydroxylation of 1,2-allenylic diphenyl phosphine oxides. Chem. Commun. 2015, 51 (35), 7439-7442.
Goldsmith, B. R.; Hwang, T.; Seritan, S.; Peters, B.; Scott, S. L. Rate-Enhancing Roles of Water Molecules in Methyltrioxorhenium-Catalyzed Olefin Epoxidation by Hydrogen Peroxide. J. Am. Chem. Soc. 2015, 137 (30), 9604-9616.
Gefahrenhinweise (EU): H272
May intensify fire; oxidizer.
Take any precaution to avoid mixing with combustibles. Keep/Store away from clothing/combustible materials. Wear protective gloves and eye/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Dispose of contents/container in accordance with local/regional/national/international regulations.