4011-20-5Relevant articles and documents
The reaction of cyclooctatetraene with dimethyldioxirane
Murray, Robert W.,Singh, Megh,Rath, Nigam P.
, p. 4539 - 4558 (1999)
The reaction of cyclooctatetraene with dimethyldioxirane leads to the formation of four diepoxides, three triepoxides, and two tetraepoxides. The structures of the triepoxides and tetraepoxides were confirmed by x-ray crystallographic analysis.
THE SYNTHESIS OF ENDOPEROXIDE OF CYCLOOCTATETRAENE VIA PHOTOSENSITIZED SINGLET OXYGENATION
Adam, Waldemar,Klug, Guenter
, p. 3155 - 3158 (1982)
7,8-Dioxabicyclodeca-2,4,9-triene (3), the hitherto unknown endoperoxide of cyclooctatetraene, was prepared via cycloaddition of singlet oxygen and characterized by spectroscopic and chemical means.
Novel (α,β-Epoxyalkyl)lithium Reagents via the Lithiation of Organyl-Substituted Epoxides
Eisch, John J.,Galle, James E.
, p. 4835 - 4840 (2007/10/02)
A series of epoxides bearing unsaturated organyl groups attached directly to the epoxy group was found to have sufficient kinetic acidity to undergo clean lithiation at low temperatures.Epoxides of the type is aryl, vinylic, acetylenic, alkoxycarbonyl, or cyano, were smoothly converted into by either t-BuLi or LDA in the temperature range of -80 to -115 deg C.The resulting (α,β-epoxyalkyl)lithium reagents could be transformed into a variety of substituted epoxides, such as R2C-CE(Un)-O, where E = D, R3Si, R3Sn, R, RCO, CO2H, or COH(R)2.In cases where Un is acyl, addition to the carbonyl, rather than lithiation, occurred preferentially.Attempted lithiations of aziridines and thiiranes led to extrusion of nitrogen and sulfur, respectively.Even the relatively stable intermediates generated at -90 deg C underwent carbenoid-like decomposition at higher temperatures to yield isomerization and intermolecular-insertion products.Observation of these processes gives direct corroboration of reaction mechanisms proposed for the base-promoted isomerizations of epoxides.