Aromatic substituted-phenyl epoxides

Our syntheses of these new materials showed that both hydrogenation and epoxidation occurred exclusively from the exo face of both VN and < >VX. This is consistent with extensive literature precedent for a variety of reactions on norbornenyl double bonds (9). H1 NMR spectroscopy of these materials also revealed an interesting pattern. All phenyl substituted compounds with endo imide rings (< >VN, HYVN, VNE) evidenced signals due to one of the ten aromatic protons (five on each phenyl ring) being shifted to unusually high field (6.4 +. 16). This is consistent with a field effect on a proton of one of... 

Aryl selenium compounds also form adducts with hydrogen peroxide, ArSe (O)OOH, that are able to carry out epoxidation [188,189], albeit at low rates [190,191]. Improvements can be made by substitution of the aromatic ring with electron-withdrawing trifluoromethyl groups [192], for example, to form the lizs-[3,5-Ws-(trifluoromethyl)phenyl]diselenide. 

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