Articolo in rivista, 2009, ENG, 10.1002/ejoc.200900802
Trogu, Elena; Cecchi, Luca; De Sarlo, Francesco; Guideri, Luca; Ponticelli, Fabio; Machetti, Fabrizio
Istituto di Chimica dei Composti Organo metallici del CNR Dipartimento di Chimica Ugo Schiff dell'Università di Firenze Dipartimento di Chimica dell'Unversità di Siena
Primary nitro compounds have not been employed as nitrile oxide precursors in reactions with active methylene compounds because the reagents commonly used as dehydrating agents also react with these dipolarophiles. However, the Cull-catalysed cycloaddition/condensation procedure has been shown to be viable with these substrates, leading directly to the expected polyfunctional isoxazoles provided nitro compounds with enhanced acidity ("activated") were used. In the absence of added dipolarophiles, these nitro compounds underwent self-condensation to the corresponding furoxans. However, as well as 3,4-dibenzoylfuroxan, benzoylnitromethane predominantly gave the isomer 3-benzoyl-4-nitro-5-phenylisoxazole, the structure of which was confirmed by crystallographic analysis.
European journal of organic chemistry (Print) (34), pp. 5971–5978
Nitro compounds, Isoxazoles, Organocatalysis, Copper, Enols
De Sarlo Francesco, Trogu Elena, Guideri Luca, Machetti Fabrizio
ID: 16885
Year: 2009
Type: Articolo in rivista
Creation: 2010-01-29 00:00:00.000
Last update: 2013-06-20 17:43:14.000
CNR institutes
External IDs
CNR OAI-PMH: oai:it.cnr:prodotti:16885
DOI: 10.1002/ejoc.200900802
ISI Web of Science (WOS): 000272425400012
Scopus: 70749151512