PHOTOCHEMISTRY OF N-ALKYLPYRROLIDINONES IN THE GAS-PHASE AND IN SOLUTION

The gas-phase and solution-phase photochemistry of a series of N-alkylpyrrolidinones have been studied.In both cases the chemistry observed has been exclusively those processes initiated by type I cleavage. The typeI gas-phase cleavage products, ethylene, carbon monoxide, l, 3, 5-trimethyl-s-triazene, water, N-alkylazetidine, and N-alkylpyrrole, have been shown to be directly analogous to the products obtained from cvclopentanone. For example, labeling experiments have demonstrated that N-methylpyrrole from N-methylpyrrolidinone is the analogue of peritenal from cyclopentanone. In solution, pyrroles are the only products obtained. No evidence was found for the occurrence of any type II processes even in systems in which they would be favored on the basis of the cvclopentanone analogy. The photochemistry of pyrrolidinones closely parallels that of the cyclopentanones with respect to type I processes, but not with respect to type II processes. © 1979, American Chemical Society. All rights reserved.