A number of 1-aryl-5-substituted-4,5-dihydropyrazoles 4 have been synthesised by 1,3-dipolar cycloaddition of variously substituted nitrilimines 2 onto the appropriate alkenyl dipolarophiles 3 in aqueous media and in the presence of a surfactant. Under these conditions, uncommon for the large majority of [3+2] cycloadditions, the electronic features of both the cycloaddends strongly dictate the reaction outcome. Clean and fast cycloadditions were observed between electron-rich nitrilimines and electron-poor dipolarophiles, while the reversal of the electronic features of the reactants gave poor results. Changes in surfactant concentration leads to some novel mechanistic insights

Molteni, G., Ponti, A., Orlandi, M. (2002). Uncommon aqueous media for nitrilimine cycloadditions. I. Synthetic and mechanistic aspects in the formation of 1-aryl-5-substituted-4,5-dihydropyrazoles. NEW JOURNAL OF CHEMISTRY, 26(10), 1340-1345 [10.1039/b205063c].

Uncommon aqueous media for nitrilimine cycloadditions. I. Synthetic and mechanistic aspects in the formation of 1-aryl-5-substituted-4,5-dihydropyrazoles

Orlandi, Me
2002

Abstract

A number of 1-aryl-5-substituted-4,5-dihydropyrazoles 4 have been synthesised by 1,3-dipolar cycloaddition of variously substituted nitrilimines 2 onto the appropriate alkenyl dipolarophiles 3 in aqueous media and in the presence of a surfactant. Under these conditions, uncommon for the large majority of [3+2] cycloadditions, the electronic features of both the cycloaddends strongly dictate the reaction outcome. Clean and fast cycloadditions were observed between electron-rich nitrilimines and electron-poor dipolarophiles, while the reversal of the electronic features of the reactants gave poor results. Changes in surfactant concentration leads to some novel mechanistic insights
Articolo in rivista - Articolo scientifico
Water, cycloaddition, syntetic and mechanistic aspect,
English
2002
26
10
1340
1345
none
Molteni, G., Ponti, A., Orlandi, M. (2002). Uncommon aqueous media for nitrilimine cycloadditions. I. Synthetic and mechanistic aspects in the formation of 1-aryl-5-substituted-4,5-dihydropyrazoles. NEW JOURNAL OF CHEMISTRY, 26(10), 1340-1345 [10.1039/b205063c].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/4612
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