On the Mechanism and Scope of a Novel Nitroolefin Rearrangement

Alfred Hassner, William Chau

Research output: Contribution to journalArticlepeer-review

22 Scopus citations


D-Labelling permits differentiation between three plausible mechanistic pathways in the novel transformation of vinylaziridine 1 with β-nitrostyrene 4 to nitro enamino olefin 5. The results are consistent with a retro-ene reaction proceeding under mild conditions (80°). Choice of proper substituents can guide the reaction toward formation of azepines or substituted enamines.

Original languageEnglish
Pages (from-to)1989-1992
Number of pages4
JournalTetrahedron Letters
Issue number19
StatePublished - 1982
Externally publishedYes


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