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Darstellung, Eigenschaften und Reaktivität von 2-, 3- und 4-Chloracyl(diphenyl)phosphanoxiden / Preparation, Properties and Reactivity of 2-, 3- and 4-Chloroacyl(diphenyl)phosphane Oxides

Authors
  • Lindner, Ekkehard
  • Steinwand, Michael
Type
Published Article
Journal
Zeitschrift für Naturforschung B
Publisher
Verlag der Zeitschrift für Naturforschung
Publication Date
Apr 01, 1982
Volume
37
Issue
4
Pages
407–411
Identifiers
DOI: 10.1515/znb-1982-0404
Source
De Gruyter
Keywords
License
Green

Abstract

The highly reactive chloroacyl(diphenyl)phosphane oxides RC(O)-P(O)Ph2 (2a-d, g) [R = HCCl2 (a), CCl3 (b), CH3CHCl (c), CH3CCl2 (d), ClCH2CH2 (e), CH3CHClCH2 (f), ClCH2(CH2)2 (g)] are obtained by oxidation of the thermally labile chloroacyl(diphenyl)- phosphanes RC(O)-PPh2 (1a-d, g) with molecular oxygen in ether at low temperatures. While hydrolysis leads to a complete decomposition of 2a-d, g, the oxidation of 1a, c, e-g with oxygen in the presence of HP(O)Ph2 yields the diphosphorylated alcohols RC[P(O)Ph2]2OH (3a, c, e-g). 3e, f can be interpreted as trapping products of the not isolable oxides 2e, f. In tetrachloroethene a partial transformation of 3a into the phosphinate RC[P(O)Ph2][OP(O)Ph2]H can be observed which can be followed 31P{1H}-NMR spectroscopically. In solution the alcohols 3c, e-g decompose to give HP(O)Ph2 and the corresponding phosphane oxides 2c, e-g.

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