Chemical and Pharmaceutical Bulletin p. 853 - 856 (1998)
Update date:2022-09-26
Topics: Regioselectivity Substrates Substituent Effects Catalysis Application
Yoneda, Ryuji
Araki, Lisa
Harusawa, Shinya
Kurihara, Takushi
Oxidation of 2-vinylazetidine 6a with m-chloroperbenzoic acid (mCPBA) in methylene dichloride (CH2Cl2) gave a mixture of dihydro-7H-[1,2]oxazepine 9a and the nitrone 10a. It was clarified that the former was obtained via the [2,3]-Meisenheimer rearrangement of the corresponding cis-N-oxide A, and the latter was formed by successive oxidation of the isoxazolidine 11 formed via the [I,2]-Meisenheimer rearrangement of the corresponding trans-N-oxide B.
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