Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Isoxazole Formation by Elimination of Isocyanic Acid fromΔ2-Isoxazoline-5-isocyanate
Yoshio IWAKURAShinsaku SHIRAISHIMasahiro YUYAMA
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1972 Volume 30 Issue 10 Pages 889-893

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Abstract
3-Phenyl-Δ2-isoxazoline-5-isocyanate (6) 3-phenyl-5-methyl-Δ2-isoxazoline-5-isocyanate (4) and 3-phenylisoxazole-5-isocyanate were prepared and they were treated with ethanol to give the corresponding urethans. (6) and (4) gave the corresponding isoxazoles by elimination of isocyanic acid by heating. The latter eliminates isocyanic acid at a temperature lower (>80°C) than the former (>180°C) by about 100°C.
Preparation of phenylene-bis (Δ2-isoxazoline-5-isocyanate) s was also conducted but purification by distillation has been unsuccessful. Phenylene-bis (isoxazole) s were obtained as single isolable products.
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© The Society of Syhthetic Organic Chemistry, Japan
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