Journal of the American Chemical Society p. 3024 - 3028 (1986)
Update date:2022-08-04
Topics:
Alberti, A.
Griller, D.
Nazran, A. S.
Pedulli, G. F.
The reactions between triplet diphenylcarbene and fluorenylidene with a variety of sulfides and disulfides were investigated with use of electron paramagnetic resonance (EPR) spectroscopy, laser flash photolysis, and product studies.Diphenylcarbene reacted with these substrates by a radical-like displacement mechanism.Rate constants were ca. 1E6 M-1 s-1, and the resulting thio-substituted diphenylmethyl radicals were identified by their EPR and optical spectra.By contrast, the analogous reactions of fluorenylidene had rate constants of 1E8-1E9 M-1 s-1 and proceeded by an ylide mechanism.Product studies were consistent with these results but were not sufficient in themselves to reveal these mechanistic differences.
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