Nitroalkanes are one of the most useful class of compounds for the carbon-carbon bond formation. , Recently, the possibility for the nitro-group to act both as electron-withdrawing and leaving group has been exploited for the regioselective synthesis of polisubstituded aromatic systems, such as methyl benzoate and diarylamine derivatives. Here we wish to report a new, three steps synthesis of polyfunctionalized phenols starting from 1,3-dinitroalkanes (1). The latter compounds can be converted into dinitrocyclohexanols 2 by their reaction with acrolein under basic conditions (neat Al2O3); treatment of 2 with potassium carbonate, followed by acidic work up, gives nitrocyclohexenones 3, which in turn can be converted into substituted phenol (4) by treatment with pheniltrimethylammonium tribromide

Synthesis of Highly Substituted Phenols from 1,3-Dinitroalkanes

PALMIERI, Alessandro;BARBONI, Luciano
2006-01-01

Abstract

Nitroalkanes are one of the most useful class of compounds for the carbon-carbon bond formation. , Recently, the possibility for the nitro-group to act both as electron-withdrawing and leaving group has been exploited for the regioselective synthesis of polisubstituded aromatic systems, such as methyl benzoate and diarylamine derivatives. Here we wish to report a new, three steps synthesis of polyfunctionalized phenols starting from 1,3-dinitroalkanes (1). The latter compounds can be converted into dinitrocyclohexanols 2 by their reaction with acrolein under basic conditions (neat Al2O3); treatment of 2 with potassium carbonate, followed by acidic work up, gives nitrocyclohexenones 3, which in turn can be converted into substituted phenol (4) by treatment with pheniltrimethylammonium tribromide
2006
6th Italian-Spanish Symposium on Organic Chemistry (ISSOC 2006)
274
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/110833
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