Journal of the American Chemical Society p. 6631 - 6635 (1982)
Update date:2022-08-04
Topics:
Wong, P. C.
Griller, D.
Scaiano, J. C.
Fluorenylidene addds to aliphatic ketones to give carbonyl ylide intermediates.With acetone, for example, laser flash photolysis experiments showed that the rate constant for this reaction was 1 x 107 M-1 s-1 in acetonitrile solvent.The resulting carbonyl ylide had an absorption spectrum with λmax = 640 nm in the absence of quenchers underwent ring closure to the corresponding oxirane.The lifetimes, τy, for the ring closure reaction are described by the equation -log(τy/s) = (13.26 +/- 0.11) - (10.96 +/- 0.12) / θ where θ = 2.3RT kcal mol-1.The spectra of the carbonyl ylides could be quenched with rate constants of circa 107 M-1 s-1 by electron-deficient olefins or oxygen.
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