Tetracyanoethylene oxidation with hydrogen peroxide

Tetracyanoethylene oxide [3189-43-3] (8), oxiranetetracarbonitnle, is the most notable member of the class of oxacyanocarbons (57). It is made by treating TCNE with hydrogen peroxide in acetonitrile. In reactions unprecedented for olefin oxides, it adds to olefins to form 2,2,5,5-tetracyanotetrahydrofuran [3041-31-4] in the case of ethylene, acetylenes, and aromatic hydrocarbons via cleavage of the ring C—C bond. The benzene adduct (9) is 3t ,7t -dihydro-l,l,3,3-phthalantetracarbonitrile [3041-36-9], C22HgN O. 

Dihydrobenzo[c]selenophene (117) forms a 1,1-adduct with bromine and an oxide on treatment with hydrogen peroxide. Both derivatives are transformed into benzo[c]selenophene (5) on suitable treatment with base the latter unstable compound forms a stable Diels-Alder adduct with tetracyanoethylene (76JA867). More vigorous oxidation of (117) with peracetic acid yields the diselenide (118). 

---