Abstract
3-Aryl-3-bromopropanoyl chloride in either ether or carbon tetrachloride reacted with 2 equiv. of hydroxylamine in the absence of trimethylsilyl chloride at ambient temperature to give directly 2,5-diarylisoxazolidin-3-ones in good yields. However, when 3-benzylhydroxylamine at $0^{\circ}C$, N-benzyl-3-bromo-3-phenylpropanohydroxamic acid (72%) and N-benzyl-C-phenylnitrone (12%) were obtained. On the contrary, 3-phenylisoxazolidin-5-one (41%) and 2-benzyl-S-phenyl-isoxzolidin-3-one (38%) were obtained when 3 equiv. of benzylhydroxylamine was used under the same conditions.
염화 삼메틸규소를 첨가하지 않고 에테르나 사염화탄소 중의 3-Aryl-3-bromopropanoyl chloride를 상온에서 2당량의 히드록실아민과 반응시켜 2,5-diarylisoxazolidin-3-ones 을 좋은 수율로 얻을 수 있었다. 그러나 $0^{\circ}C$에서 3-bromohydrocinnamoyl chloride 는 2당량의 벤질히드록실아민과 반응하여 N-benzyl-3-bromo-3-phenylpropanohydroxamic acid (72%) 와 N-benzyl-C-phenylnitrone (12%)을 생성하며 같은 조건하에서 3당량의 벤질히드록실아민을 사용하면 3-phenylisoxazolidin-5-one (41%) 과 2-benzyl-S-phenyl-isoxzolidin-3-one (38%)이 생성된다.
