141525-28-2Relevant articles and documents
Microwave accelerated cycloaddition reactions of nitrile oxides and allylic alcohols
Lu, Ta-Jung,Tzeng, Gwo-Ming
, p. 189 - 196 (2007/10/03)
The application of microwaves in promoting the cycloaddition reactions of allyl alcohols with nitrile oxides using a domestic microwave oven and a focused monomode microwave reactor have demonstrated that not only was the reaction time substantially reduced, but also the reaction yields were significantly improved over the conventional stirred reactions. Microwave irradiation alters the regioselectivity of the cycloaddition reaction which favors the non-hydrogen-bond directed cycloadduct, isoxazoline 4.
Regiocontrol of Nitrile Oxide Cycloadditions to Allyl Alcohols. Synthesis of 4-Substituted and 4,4-Disubstituted 5-Hydroxymethyl-2-isoxazolines
Kanemasa, Shuji,Nishiuchi, Masaki,Wada, Eiji
, p. 1357 - 1360 (2007/10/02)
The first regiocontrol of nitrile oxide cycloadditions is described.Reaction of benzonitrile oxide with (E)-2-butenol is highly accelerated by the presence of a magnesium alkoxide, and this reaction proceeds in an exclusively regioselective manner to produce 5-hydroxymethyl-4-methyl-3-phenyl-2-isoxazoline as the sole cycloadduct.Synthetic applications to other substituted allyl alcohols are discussed.