Studies on the [2,3]-Meisenheimer rearrangement of 2-vinylazetidine N- oxides

DOI: 10.1248/cpb.46.853

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 853 - 856 (1998)

Update date:2022-09-26

Topics: Regioselectivity Substrates Substituent Effects Catalysis Application

Authors:

Yoneda, Ryuji

Araki, Lisa

Harusawa, Shinya

Kurihara, Takushi

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Article abstract of DOI:10.1248/cpb.46.853

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.

Full text of DOI:10.1248/cpb.46.853

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