An unexpected highly stereoselective bisaziridination of (E,E)-1,4-dialkyl-2,3-dinitrobutadienes followed by a nitro group driven ring enlargement

A direct aza-MIRC (Michael initiated ring closure) reaction on (E,E)-1,4-dialkyl-2,3-dinitro-l,3-butadienes under very mild conditions was performed to obtain ([plusmn])-2,2'-dinitro-2,2'-biaziridines. A simple reaction with sodium iodide in d imethyl sulfoxide ( DMSO), with an unforeseen regioselective aziridine C-C cleavage was performed to achieve ring enlargement of 3,3'-bi(1,2,4-oxadiazole) derivatives.