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Photochemistry of methylenenitrones and related compounds. A study of oxaziridine and nitrene formation

1976; Wiley; Volume: 13; Issue: 5 Linguagem: Inglês

10.1002/jhet.5570130513

1943-5193

Melvin L. Druelinger, Robert W. Shelton, S. R. Lammert,

Organic Chemistry Cycloaddition Reactions

Abstract A series of N ‐alkylmethylenenitrones has been prepared and can be irradiated cleanly to simple N ‐alkyloxaziridines. Further irradiations of these systems lead to N ‐alkylformamides via a singlet state rearrangement process. Triplet state fragmentation to give amines, presumably via alkyl nitrenes, has been observed but with very low efficiency. Only N ‐aryl systems appear to lead to significant nitrene formation.