The Journal of Organic Chemistry

Is oxygen abstraction by nucleophilic reagents a characteristic reaction of oxaziridines?

Y Hata, M Watanabe

Index: Hata, Yoshiteru; Watanabe, Masamichi Journal of Organic Chemistry, 1981 , vol. 46, p. 610 - 614

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Citation Number: 37

Abstract

The reaction of oxaziridines with nucleophilic reagents was studied. The summarized results are as follows.(1) The nucleophilic reactions occur preferentially on the nitrogen atom and the oxaziridine decomposes into a carbonyl compound and an ylide.(2) The reaction site shifts from nitrogen toward oxygen as the bulk of the ring substituents increases.(3) Cis isomers show faster reaction than trans isomers.(4) The carbon atom of the oxaziridine ...