DEPMPO and lipophilic analogues: synthesis and EPR studies

DEPMPO and lipophilic analogues: synthesis and EPR studies DEPMPO (5-diethylphosphono-5-methyl-1-pyrroline N-oxide) is now recognised as a major trap for the applications of spin-trapping techniques in biological milieu. We report herein a new synthetic route for DEPMPO ending with the reductive cyclisation of the phosphorylated γ-nitroaldehyde 8. In comparison with the usual synthesis of DEPMPO, involving the oxidation of the parent pyrrolidine 3, the new approach avoids the formation of over oxidation by-products thus making easier the purification of DEPMPO. Lipophilic analogues of DEPMPO have been prepared through addition of various Y2P(O)H on 2-methyl-1-pyrroline, followed by oxidation of the ensuing pyrrolidines. These new nitrones were used to trap different radicals in water and organic solvents. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

DEPMPO and lipophilic analogues: synthesis and EPR studies

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Publisher
Springer Journals
Copyright
Copyright © 2002 by VSP 2002
Subject
Chemistry; Inorganic Chemistry; Physical Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1163/156856702320267091
Publisher site
See Article on Publisher Site

Abstract

DEPMPO (5-diethylphosphono-5-methyl-1-pyrroline N-oxide) is now recognised as a major trap for the applications of spin-trapping techniques in biological milieu. We report herein a new synthetic route for DEPMPO ending with the reductive cyclisation of the phosphorylated γ-nitroaldehyde 8. In comparison with the usual synthesis of DEPMPO, involving the oxidation of the parent pyrrolidine 3, the new approach avoids the formation of over oxidation by-products thus making easier the purification of DEPMPO. Lipophilic analogues of DEPMPO have been prepared through addition of various Y2P(O)H on 2-methyl-1-pyrroline, followed by oxidation of the ensuing pyrrolidines. These new nitrones were used to trap different radicals in water and organic solvents.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 13, 2004

References

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