The influence of solvent viscosity and reaction temperature upon the stereoselectivity and intramolecularity of the Stevens [1,2] rearrangement of the ylide (1) has been examined; the results are compatible with two possible mechanisms: (i) a radical pair mechanism with an average geminate recombination rate which is exceptionally fast, or (ii) dual pathways involving concurrent radical pair and concerted processes.
W. D. Ollis, M. Rey, I. O. Sutherland and G. L. Closs, J. Chem. Soc., Chem. Commun., 1975, 543 DOI: 10.1039/C39750000543
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