Journal of the American Chemical Society

Thermolysis of bis [2-[(trimethylsilyl) oxy] propyl] furoxan (TOP-furoxan). The first practical method for intermolecular cycloaddition of an in situ generated nitrile oxide …

DP Curran, CJ Fenk

Index: Curran,D.P.; Fenk,C.J. Journal of the American Chemical Society, 1985 , vol. 107, p. 6023

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Citation Number: 33

Abstract

Abstract: Cycloaddition of in situ generated nitrile oxides with 1, 2-di-and trisubstituted olefins to form A*-isoxazolines is problematical due to dimerization of the nitrile oxides to form furoxans. It has been found that thermolysis of bis [2-[(tri-methylsilyl) oxy] prop-2-yl] furoxan (TOP-furoxan)(7) in the presence of 1-2 equiv of mono-, di-, and trisubstituted olefins (165" C, $ H) produces the derived isoxazolines 9a-t in good to excellent yields. Evidence ...