
Journal of the Chemical Society. Perkin transactions II p. 243 - 253 (1993)
Update date:2022-08-04
Topics:
Takahashi, Yasutake
Wakamatsu, Kan
Morishima, Shin-ichi
Miyashi, Tsutomu
Derivatives of 1,2-dioxacyclohex-4-ene and 2,3-dioxabicyclo<2.2.2>oct-5-ene (endoperoxides, EPs) form EDA complexes with tetracyanoethylene (TCNE).The phenyl-substituted EPs 3a, 4a, 4b and 6 undergo electron-transfer-induced reactions when the EDA complexes are irradiated.Two types of reactions are observed depending on the ring system.Monocyclic EPs (3a, 4a and 4b) afford furan derivatives, possibly through the Criegee-type rearrangement, and dehydration, whereas the bicyclic EP 6 undergoes cycloreversion through the C-O bond cleavage.
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