ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 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.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19760590730
