A new synthesis of 2-methyleneaziridines

Norbert De Kimpe, Dirk De Smaele, Zsolt Sakonyi

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

A new synthetic route leading to 2-methyleneaziridines has been developed by base-induced 1,2-dehydrobromination of 2-(bromomethyl)aziridines. Several base-solvent pairs did not lead to 2-methyleneaziridines. Only potassium tert-butoxide in tetrahydrofuran afforded 2-methyleneaziridines in competition with the substitution products, i.e. 2-(tert-butoxymethyl)aziridines. Various attempted functionalizations of 1-(arylmethyl)-2-methyleneaziridines failed, but they proved to be excellent substrates for the synthesis of β-lactam derivatives, i.e. 1-(arylmethyl)-2-iminoazetidines, through ring expansion with azides carrying electron-withdrawing substituents.

Original languageEnglish
Pages (from-to)2448-2452
Number of pages5
JournalJournal of Organic Chemistry
Volume62
Issue number8
DOIs
Publication statusPublished - Jan 1 1997

ASJC Scopus subject areas

  • Organic Chemistry

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