Journal of the American Chemical Society p. 6863 - 6871 (1986)
Update date:2022-08-05
Topics:
Nelsen, Stephen F.
Kapp, Daniel L.
Akaba, Ryoichi
Evans, Dennis H.
Cyclic voltammetry studies allow estimation of the rate constant for addition of O2 to biadamantylidene cation radical (1.+) to be 5600 M-1 s-1 at room temperature and for the cleavage of biadamantylidene dioxetane cation radical to oxygen and 1.+ > 800 s-1.Chlorination of the adamantane skeleton slows the overall rate of oxygen addition, and the face selectivity for oxygenation of 5(Cl) is 25:1 in favor attack from the olefin face syn to the chlorine.The implications of these findings for the mechanism of the reaction are discussed.
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