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 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.