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Titolo:
Beckmann rearrangement of OTDP salts of oximes of aromatic ketones and synthetic applications
Autore:
Thiebaut, S; Gerardin-Charbonnier, C; Selve, C;
Indirizzi:
Univ54506y 1, Lab Chim Phys Organ & Colloidale, INCM, UMR CNRS UHP 7565, F- Univ Nancy 1 Vandoeuvre Nancy France F-54506 INCM, UMR CNRS UHP 7565, F-
Titolo Testata:
TETRAHEDRON
fascicolo: 5, volume: 55, anno: 1999,
pagine: 1329 - 1340
SICI:
0040-4020(19990129)55:5<1329:BROOSO>2.0.ZU;2-7
Fonte:
ISI
Lingua:
FRE
Soggetto:
BIOACTIVE SURFACTANTS;
Keywords:
Beckmann rearrangement; oximoxy-tris-(dimethylamino)-phosphonium salts; amidines; glycosylation;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
23
Recensione:
Indirizzi per estratti:
Indirizzo: Selve, C Univ Nancy 1, Lab Chim Phys Organ & Colloidale, INCM, UMR CNRS UHP 7565, BP Univ Nancy 1 BP 239 Vandoeuvre Nancy France F-54506 UHP 7565, BP
Citazione:
S. Thiebaut et al., "Beckmann rearrangement of OTDP salts of oximes of aromatic ketones and synthetic applications", TETRAHEDRON, 55(5), 1999, pp. 1329-1340

Abstract

Reaction between tris(dimethylamino)-phosphine, carbon tetrachloride and oximes of ketones leads to the corresponding Oximoxy-Tris-(Dimethylamino)-Phosphonium salts (OTDP salts), which are isolated in the form of hexafluorophosphates. These salts are solid and stable except if they are completely dehydrated. Their solutions, in non polar solvents like CHCl3, give Beckmannrearrangement at room temperature. The kinetics and mechanism have been studied by NMR. We have defined the conditions of trapping of the cationic intermediates formed in the rearrangement, leading to an effective synthesis of amidines and an access to a glycoside structure using the hemiacetalic hydroxyl group of sugar as nucleophile. (C) 1999 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 18/11/17 alle ore 05:51:47