Ketone- and ester-substituted diazo compounds, which contain a pyrrolidine moiety were treated with dirhodium tetraacetate generating the corresponding rhodium carbenoids. They were expected to insert into a C H bond of the pyrrolidine moiety but reacted differently. The ketone-substituted rhodium carbenoid underwent a Wolff rearrangement. The resulting ketene continued to react by lactamization and electrocyclic ring-opening and gave an acrylamide. The ester- ...
