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The Reaction of Singlet and Triplet Oxygen with 2‐Phenylnorbornene
Author(s) -
Jefford Charles W.,
Boschung André F.,
Rimbault Christian G.
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590730
Subject(s) - chemistry , singlet oxygen , trimer , singlet state , solvent , epoxide , methanol , photochemistry , ketone , oxygen , polymer chemistry , organic chemistry , excited state , catalysis , dimer , physics , nuclear physics
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.