(+/-)-2,2'-Dinitro-2,2'-biaziridines were obtained by a direct aza-MIRC (Michael initiated ring closure) reaction on (E,E)-1,4-dialkyl-2,3-dinitro-1,3-butadienes under very mild conditions. The reactions occur with high stereoselectivity as shown by the enantioselective HPLC analyses performed on the crude mixtures. Ring enlargement to 3,3'-bi(1,2,4-oxadiazole) derivatives was easily obtained by a simple treatment with sodium iodide in DMSO, with an unforeseen regioselective aziridine C-C cleavage.
An Unexpected Highly Stereoselective Bisaziridination of (E,E)-1,4-Dialkyl-2,3-dinitrobutadienes Followed by a Nitro Group Driven Ring Enlargement / Ciogli, Alessia; Fioravanti, Stefania; Gasparrini, Francesco; Pellacani, Lucio; Egon, Rizzato; Domenico, Spinelli; Tardella, Paolo Antonio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 74:24(2009), pp. 9314-9318. [10.1021/jo902112j]
An Unexpected Highly Stereoselective Bisaziridination of (E,E)-1,4-Dialkyl-2,3-dinitrobutadienes Followed by a Nitro Group Driven Ring Enlargement
CIOGLI, Alessia;FIORAVANTI, Stefania;GASPARRINI, Francesco;PELLACANI, Lucio;TARDELLA, Paolo Antonio
2009
Abstract
(+/-)-2,2'-Dinitro-2,2'-biaziridines were obtained by a direct aza-MIRC (Michael initiated ring closure) reaction on (E,E)-1,4-dialkyl-2,3-dinitro-1,3-butadienes under very mild conditions. The reactions occur with high stereoselectivity as shown by the enantioselective HPLC analyses performed on the crude mixtures. Ring enlargement to 3,3'-bi(1,2,4-oxadiazole) derivatives was easily obtained by a simple treatment with sodium iodide in DMSO, with an unforeseen regioselective aziridine C-C cleavage.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
