117985-05-4Relevant articles and documents
Nitrone/Imine Selectivity Switch in Base-Catalysed Reaction of Aryl Acetic Acid Esters with Nitrosoarenes: Joint Experimental and Computational Study
Volpe, Chiara,Meninno, Sara,Roselli, Angelo,Mancinelli, Michele,Mazzanti, Andrea,Lattanzi, Alessandra
, p. 5457 - 5466 (2020)
Herein we report a mild and diastereoselective access to ketonitrones by reacting easily available aryl acetic acid esters and other active methylene compounds, with nitrosoarenes under catalytic loading of 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) at room temperature. Depending on the substitution pattern and nature of the aryl moiety, a switch toward the formation of imines can be observed. The mechanistic framework is put to scrutiny by experimental and theoretical studies, pointing to the formation of a nitroso aldol intermediate, whose fate toward one of the competing pathways, namely hydride transfer or elimination, would depend upon the NOH/CHα relative acidities. (Figure presented.).
Heterocycles with Potential Heterodienes. I. A New Synthesis of 3-Methyl-1-phenyl-4-phenylazomethine-5-pyrazolone: Comparison with Other Synthetic Routes
Tacconi, G.,Marinoni, G.,Righetti, P. P.,Desimoni, G.
, p. 674 - 678 (2007/10/02)
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