Abstract
Suitably substituted aziridines and oxiranes undergo electrocyclic ring opening to form small equilibrium concentrations of azomethine ylides or carbonyl ylides, respectively, in analogy with the conversion of the isoelectronic cyclopropyl anion to the allyl anion. The azomethine ylides and carbonyl ylides are 1.3-dipoles which can be intercepted by cycloaddition to dipolarophiles. The steric course of the thermal and photochemical ring opening of aziridines and oxiranes as well as some structure-rate relationships have been established. In the case of dimethyl cis- and trans-1-(p-methoxy-phenyl)aziridine-2.3-dicarboxylates, the total energy profile for ring opening and stereoisomerization of the azomethine ylides has been elaborated by kinetic and flash-photolytic techniques,
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