Issue 11, 1991

Synthesis and radical-addition stereochemistry of two trimethyl-1-pyrroline 1-oxides as studied by EPR spectroscopy

Abstract

A two-step synthetic route has been applied to the preparation of two five-membered ring nitrone spin traps, 3,5,5-trimethyl-1-pyrroline 1-oxide (3-Me-DMPO) and 4,5,5-trimethyl-1 -pyrroline 1-oxide (4-Me-DMPO). A general method has been developed for the purification of the aqueous nitrone solution, which is suitable for the trapping of radicals present in biological processes. The EPR spin-trapping stereochemistry of 3- and 4-Me-DMPO has been investigated. The addition of the radicals ˙OH, RC˙HOH, tetrahydrofuranyl and ˙OBut, to Me-DMPO is stereoselective or stereospecific. Hydrogen atom addition to 3-Me-DMPO and 4-Me-DMPO gives aminoxyls 9 and 10, respectively, which each contain two non-equivalent β-protons.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1991, 1855-1860

Synthesis and radical-addition stereochemistry of two trimethyl-1-pyrroline 1-oxides as studied by EPR spectroscopy

Y. Zhang, D. Lu and G. Xu, J. Chem. Soc., Perkin Trans. 2, 1991, 1855 DOI: 10.1039/P29910001855

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