58007-45-7Relevant articles and documents
On the Reaction of Phenyldisic Acids with α,β-Unsaturated Carbonyl Compounds. Reversible Non-Catalyzed Michael Addition and Ring Closure to Derivatives of 2H,7H-Isoxazolooxazine
Zvilichovsky, Gury,David, Mordechai,Nemes, Eliahu
, p. 299 - 304 (2007/10/02)
4-Aryl-3,5-dihydroisoxazoles which are strong organic acids add spontaneously to mesityl oxide to form 4-aryl-2-(1,1-dimethyl-3-oxobutyl)isoxazolidine-3,5-dione.This reaction was found to be reversible and the equilibrium is solvent dependent.These acids add to 2 moles of methyl vinyl ketone.The adducts obtained from mesityl oxide undergo ketalization to form derivatives of 2H,7H-isoxazolooxazine on exposure to alcohols.The rate of this ring closure reaction is dependent on the nature of the alcohol and on the nature of the substituent on the phenyl group which is at position 4 of the isoxazole ring.The mechanisms of the non catalyzed Michael addition and of the ketalization reaction are discussed.The structure of the polymers which are obtained by the reaction of phenyldisic acids with acrolein and crotonaldehyde is also discussed.