The Cycloaddition of Vinylaziridines with Unsaturated Substrates

Alfred Hassner, William Chau, Rosario D'Costa

Research output: Contribution to journalArticlepeer-review

7 Scopus citations


Vinylaziridines undergo ring expansion reactions which in case of divinylaziridines lead to dihydroazepines. Addition of 2‐phenyl‐2‐vinyl‐aziridine 10a to dimethyl acetylene dicarboxylate provides a facile method of in situ generation of a divinylaziridine and leads to isolation of an azepine derivative. Likewise we show that cycloaddition of 10a proceeds even with olefinic nitriles, sulfones and esters with formation of tetrahydroazepines. However, when the substrates are unsaturated nitro compounds or ketones, a novel rearrangement to open chain enamine derivatives takes place. Deuterium labelling in the β‐nitrostyrene substrate and in the vinylaziridine provide evidence for a retro‐ene reaction mechanism leading to the rearrangement. These data provide a framework for assessing the factors that guide the reactions either towards formation of seven‐membered ring azepine derivatives or toward open‐chain rearranged products.

Original languageEnglish
Pages (from-to)76-81
Number of pages6
JournalIsrael Journal of Chemistry
Issue number1
StatePublished - 1982
Externally publishedYes


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