| Abstract
| - A new synthetic route leading to 2-methyleneaziridines has beendeveloped by base-induced 1,2-dehydrobromination of 2-(bromomethyl)aziridines. Severalbase-solvent pairs did not lead to2-methyleneaziridines. Only potassium tert-butoxide intetrahydrofuran afforded 2-methyleneaziridines in competition with the substitution products,i.e.2-(tert-butoxymethyl)aziridines.Various attempted functionalizations of1-(arylmethyl)-2-methyleneaziridines failed, but theyprovedto be excellent substrates for the synthesis of β-lactam derivatives,i.e. 1-(arylmethyl)-2-iminoazetidines, through ring expansion with azides carryingelectron-withdrawing substituents.
|
