Oxidative ring-opening of aziridine-1-carboxylates with sulphoxides

Citations of this article
Mendeley users who have this article in their library.
Get full text


The title reaction furnishes a practical preparation of α-carbalkoxyamino ketones from nitrene adducts of the corresponding olefins. The aziridines are alternatively accessible via addition,of iodine isocyanate, alcoholysis and elimination of hydrogen iodide. DMSO-cleavage of cis and trans isomers of 1-carbethoxy-2-methyl-3-phenylaziridine proceeds regioselectively: the cis isomer reacts at 1,2-bond and 1,3-bond in a ratio of ca 1:1, whereas the trans isomer reacts at 1,3-bond almost exclusively. The 1,3-bond cleavage is predominant under acidic conditions for both isomers. Under neutral conditions, the cleavage proceeds via an SN2 type transition state. © 1970.




Fujita, S., Hiyama, T., & Nozaki, H. (1970). Oxidative ring-opening of aziridine-1-carboxylates with sulphoxides. Tetrahedron, 26(18), 4347–4352. https://doi.org/10.1016/S0040-4020(01)93080-7

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free