Issue 5, 1986

The photoelimination of N-nitroso-N-acetyl-α-amino acids; a new synthesis of 1,2,4-oxadiazoles

Abstract

The excitation of N-nitroso-N-acetyl-α-amino acids, nitrosopeptide model compounds, under neutral and weakly basic conditions, caused the homolysis of the N–N bond followed by decarboxylation to give hyponitrous acid (HNO) and N-acetylimines which were susceptible to nucleophilic addition. While weak bases caused the carboxylate group to assist intramolecular rearrangement to a small extent, they functioned primarily to provide nucleophilic NO, which initiated nucleophilic attack leading to the C-nitroso derivatives. These C-nitroso derivatives spontaneously cyclized to 1,2,4-oxadiazoles much more rapidly than tautomerism to the corresponding oximes; the latter oximes failed to cyclize under the basic conditions.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1986, 727-733

The photoelimination of N-nitroso-N-acetyl-α-amino acids; a new synthesis of 1,2,4-oxadiazoles

Y. L. Chow and J. S. Polo, J. Chem. Soc., Perkin Trans. 2, 1986, 727 DOI: 10.1039/P29860000727

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements