Abstract
A set of azetidinium ions substituted at the nitrogen atom either by a benzyl group or a benzhydryl group were synthesized to delineate the scope of their ring expansion into 2-phenyl- or 2,2-diaryl-pyrrolidines through a Stevens rearrangement. Whereas the regioselectivity of the rearrangement is very high, the diastereoselectivity is low when 2,3-disubstituted pyrrolidines are produced, except in one case. The major undesirable side-reaction is a Hofmann elimination leading to ring cleavage.
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