Journal of Organic Chemistry p. 4879 - 4881 (1982)
Update date:2022-08-17
Topics:
Nelsen, Stephen F.
Qualy, Richard J.
Gannett, Peter M.
The ease of one-electron oxidation is compared for ? coupled and non-?-coupled γ-oxopiperidine nitroxides and their saturated analogues (CO -> CH2).For the non-?-coupled pair, 1,3,3-trimethyl-2-oxyl-2-azabicyclo<2.2.2>octan-5-one (9) has IPv = 7.29 eV, Eo' = 0.73 V and its CO -> CH2 analogue 11 IPv = 6.88, Eo' = 0.52 V.The ?-coupled pair 9-oxyl-9-azabicyclo<3.3.1>nonan-3-one (12) has IPv = 7.78 eV, Eo' = 0.83 V and its CO -> CH2 analogue 13 IPv = 7.39 eV, Eo' = 0.58 V.Replacement of CO by CH2 in the non-?-coupled example has as large an effectof IPv and only a 13percent smaller effect on Eo' than in the ?-coupled example, making it appear that a ?-coupled transmission of positive charge from the nitrogen to the carbonyl in the radical cation is unimportant.
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