Elemental white phosphorus as a radical trap: a new and general route to phosphonic acids
Barton, Derek H. R.; Zhu, Jieping
1993

Abstract

White phosphorus is a very efficient trap for carbon radicals generated by white light photolysis of Barton PTOC esters using CH2Cl2-CS2 as solvent at 0 Deg under dry argon. Removal of the solvent mixt. and oxidn. with H2O2 in 1,2-dimethoxyethane provides an efficient new synthesis of phosphonic acids, where this function replaces the carboxyl in the original carboxylic acid. [on SciFinder (R)]

Details

Title Elemental white phosphorus as a radical trap: a new and general route to phosphonic acids
Author(s) Barton, Derek H. R. ; Zhu, Jieping
Published in Journal of the American Chemical Society
Volume 115
Issue 5
Pages 2071-2
Date 1993
ISSN 0002-7863
Keywords
Note CAN 119:8875
29-7
Organometallic and Organometalloidal Compounds
Dep. Chem.,Texas A and M Univ.,College Station,TX,USA.
Journal
written in English.
89025-67-2; 91233-19-1; 105398-69-4; 114050-31-6; 147986-70-7 Role: RCT (Reactant), RACT (Reactant or reagent) (photolysis of, in presence of white phosphorus, phosphonic acid deriv. from); 1005-23-8P; 4672-30-4P; 5137-73-5P; 23906-88-9P; 147986-71-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 12185-10-3 (White phosphorus) Role: USES (Uses) (radical trapping by, of carbon radicals)
DOI https://doi.org/10.1021/ja00058a082
Laboratories LSPN
Record Appears in Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date 2010-11-25