Editing Epoxide (section)

===Organic peroxides and metal catalysts===
Metal complexes are useful catalysts for epoxidations involving [[hydrogen peroxide]] and alkyl hydroperoxides. Metal-catalyzed epoxidations were first explored using [[tert-butyl hydroperoxide]] (TBHP).<ref name=name2>{{cite journal | year = 1965 | title =  Metal Acetylacetonate Catalyzed Epoxidation of Olefins with t-Butyl Hydroperoxide| journal =  The Journal of Organic Chemistry| volume = 30 | issue = 6| page = 2074 | doi = 10.1021/jo01017a520 | last1 = Indictor| first1 = Norman}}</ref>  Association of TBHP with the metal (M) generates the active metal peroxy complex containing the MOOR group, which then transfers an O center to the alkene.<ref>{{cite journal | author = Thiel W. R. | year = 1997 | title = Metal catalyzed oxidations. Part 5. Catalytic olefin epoxidation with seven-coordinate oxobisperoxo molybdenum complexes: A mechanistic study | journal = Journal of Molecular Catalysis A: Chemical| volume = 117 | issue = 1–3 | pages = 449–454 | doi = 10.1016/S1381-1169(96)00291-9 }}</ref>
:[[File:SimpleMOORexpxCyc2.svg|thumb|left|Simplified mechanism for metal-catalyzed epoxidation of alkenes with peroxide (ROOH) reagents]]
[[Vanadium(II) oxide]] catalyzes the epoxidation at specifically less-substituted alkenes.<ref>{{cite journal|date=25 Sep 2006|first=Douglass|last=Taber|title=Selective reactions of Alkenes|journal=Organic Chemistry Highlights|url=https://www.organic-chemistry.org/Highlights/2006/25September.shtm}}</ref>