Abstract
AbstractThe reaction of singlet oxygen with 2‐phenylnorbornene (1) in aprotic solvents gives 3‐formylcyclopentyl phenyl ketone (2) (10%) and uncharacterized polymer (90%). When methanol is used as solvent, endo‐2‐phenyl‐exo‐2‐methoxy‐exo‐3‐hydroperoxynorbornane (4) and endo‐2‐(anti‐1′, 4′‐epidioxy‐5′,6′‐epoxycyclohex‐2′‐enyl)‐exo‐2,3‐epoxynorbornane (6 and 7) are obtained in addition to 2. Triplet oxygen with 1 gave 2, endo‐2‐phenyl‐exo‐2,3‐epoxynorbornane (8), and the trimer 9 or 10 of exo‐2,3‐epidioxy‐endo‐2‐phenylnorbornane. With protic solvents the amount of epoxide increased at the expense of trimer. The singlet and triplet oxygen reactions are discussed in the light of possible intermediates.
Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
