Journal of the American Chemical Society p. 10611 - 10620 (1993)
Update date:2022-08-04
Topics:
Nelsen, Stephen F.
Chen, Ling-Jen
Petillo, Peter A.
Evans, Dennis H.
Neugebauer, Franz A.
The N-isopropylated hydrazine radical cations from 7 (22/tBu,iPr) and 9 (22/iPr2) are isolable and are the first examples of isolable hydrazine radical cations which lack all Cα-H bonds being protected as bridgehead carbons in bicyclic rings. The cyclic voltammogram of 9 shows electrochemically irreversible oxidation and reduction waves at platinum. It is argued that this results from a gearing effect of the isopropyl groups, which causes the radical cation from neutral 9 to be generated in an unstable conformation. Kinetic and thermodynamic conformational effects which cause hydrazine cyclic voltammetry curves to be electrochemically irreversible are contrasted.
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