Abstract
This chapter discusses the reaction of (1) isoxazoles, (2) isoxazol ines, (3) isoxazolidines, (4) oxazoles, (5) oxazolines and oxazolinones, (6) oxazolidines and oxazolidinones, and (7) oxad iazoles. The reaction of arylcyclopropanes I with sodium nitrite in trifluoroacetic acid affords isoxazoles 2 quantitatively; in contrast, l,l-dichloro-2-phenylcyclopropane yields only 13% of 3-chloro-5-phenylisoxazole 3 in this reaction. Carboxylic acids react at room temperature or below with β-amino alcohols in the presence of triethylamine and Ph 3 PCl 2 , generated in situ from triphenylphosphine and carbon tetrachloride, to give 2-substituted 2-oxazolines, for example 32, in up to 80% yield; o-aminophenols are similarly converted into benzoxazoles 33. The reaction of (chloromethyl)oxirane with phenyl isocyanate to give the oaazolidinone 53 is catalyzed by late rare earth chlorides such as, erbium, ytterbium, and yttrium chlorides.
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