Oxidative cleavage of the C=N bond during singlet oxygenations of amidoximates

Authors
Ocal, N Erden, I
Citation
N. Ocal et I. Erden, Oxidative cleavage of the C=N bond during singlet oxygenations of amidoximates, TETRAHEDR L, 42(29), 2001, pp. 4765-4767
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
29
Year of publication
2001
Pages
4765 - 4767
Database
ISI
SICI code
0040-4039(20010716)42:29<4765:OCOTCB>2.0.ZU;2-G
Abstract
Amidoximes are inert toward singlet oxygen (O-1(2)), however, the photooxyg enation of amidoximate anions proceeds smoothly and in high yield to give m ixtures of amides and nitriles. The mechanism of these reactions appeals to involve carbonyl oxide intermediates. The oxidative cleavage of amidoximat es closely resembles the results obtained from nitric oxide synthase (NOS) oxidations of N-hydroxyarginine. (C) 2001 Elsevier Science Ltd. All rights reserved.