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Abstract
The synthesis of a functionalized calix[4]arene bearing 1,3-dipolaric nitrone groups (5) has been carried out. The reaction of N-methylhydroxylamine or N-propylhydroxylamine with the carbonyl group of 5,11,7,23-tetraformyl-25,26,27,28-tetraalkoxycalix[4]arene leads to calix[4]arenes bearing a nitrone function at each of the four para-positions. Via 1,3-dipolar cyclo-addition of acrylic acid methyl ester with the nitrone functions of 5, subsequently an upper rim-substituted tetraisoxalidinecalix[4]arene is quantitatively synthesized. Further, the minimization of shrinkage of a dental filling depending on the amount of calix[4]arene-tetranitrone is discussed. Copyright © 2011 Society of Chemical Industry
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