Stable nitrile oxide dipolar cycloadditions in pure water

A systematic study on the behaviour of stable 2,4,6-trimethyl-3,5-dichlorobenzonitrile oxide versus a number of mono-, bi- and trisubstituted dipolarophiles in water was pursued obtaining simple as well as annulated isoxazolines. Reaction conditions changed with the dipolarophilic species, according...

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Veröffentlicht in:	Tetrahedron 2011-09, Vol.67 (38), p.7343-7347
Hauptverfasser:	Molteni, Giorgio, Del Buttero, Paola
Format:	Artikel
Sprache:	eng
Schlagworte:	Bonding Carbon-carbon composites Catalysis Catalysts: preparations and properties Chemistry Colloidal state and disperse state Cycloaddition Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Micelles. Thin films Nitriles Organic chemistry Oxides Preparations and properties Sodium Solubility Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Beschreibung
Zusammenfassung:	A systematic study on the behaviour of stable 2,4,6-trimethyl-3,5-dichlorobenzonitrile oxide versus a number of mono-, bi- and trisubstituted dipolarophiles in water was pursued obtaining simple as well as annulated isoxazolines. Reaction conditions changed with the dipolarophilic species, according to their solubility in water and the degree of substitution of the reactive carbon–carbon multiple bond. The presence of sodium dodecylsulfate was also tested as potential micellar catalyst. [Display omitted]
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2011.07.037