Studies on the [2, 3]-Meisenheimer Rearrangement of 2-Vinylazetidine N-Oxides

Ryuji YONEDA; Lisa ARAKI; Shinya HARUSAWA; Takushi KURIHARA

doi:10.1248/cpb.46.853

Ryuji YONEDA, Lisa ARAKI, Shinya HARUSAWA, Takushi KURIHARA

Author information

Keywords: Meisenheimer rearrangement, tertiary amine N-oxide, 2-vinylazetidine, [1, 2]oxazepine, m-chloroperbenzoic acid

JOURNAL FREE ACCESS

1998 Volume 46 Issue 5 Pages 853-856

DOI https://doi.org/10.1248/cpb.46.853

Details

Abstract

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 [1, 2]-Meisenheimer rearrangement of the corresponding trans-N-oxide B.

Corresponding author

Register with J-STAGE for free!