Gas-phase synthesis of N-alkenyl-3-hydroxypyrroles by sequential collapse of two dipolar intermediates
Abstract
Flash vacuum pyrolysis (FVP) of the oxazolidinylmethylene derivatives of Meldrum's acid 1 and 2 gives alkenylpyrroles 5 and 6 respectively, by a mechanism which involves collapse of a bicyclic intermediate 3; FVP of the related compound 9(which cannot undergo this process) gives the tricyclic compound 11; probably via an intramolecular Diels–Alder reaction.