Anomalous Reaction of Ethyl Bromofluoro- and Difluoro-Acetates with Dialkylphosphonites

The Michaelis-Arbuzov reaction of ethyl α -bromo-α -fluoro- and α, α -difluoro-acetates with dialkyl phenylphosphonites leads to the formation of unusual products including a fluorophosphinate. The reaction of ethyl bromofluoracetate with diisopropyl- and dimethyl-phenylphosphonites furnishes a comp...

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Published inPhosphorus, sulfur, and silicon and the related elements Vol. 183; no. 11; pp. 2655 - 2668
Main Authors Durst, H. D., Rohrbaugh, D. K., Smith, P., Nilles, J. M., Connell, T., Laramee, J. A., Munavalli, S.
Format Journal Article
LanguageEnglish
Published ABINGDON Taylor & Francis Group 07.10.2008
Taylor & Francis
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
DART mass spectrometry
dialkylphosphonites
free radical Arbuzov reaction
GC-MS
Michaelis-Arbuzov reaction
MS-MS
Physical Sciences
Science & Technology
α-fluoro- and difluoro-esters
GC-MS
ARBUZOV
Michaelis-Arbuzov reaction
alpha-fluoro- and difluoro-esters
ESTERS
free radical Arbuzov reaction
dialkylphosphonites
DART mass spectrometry
MS-MS
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Summary:The Michaelis-Arbuzov reaction of ethyl α -bromo-α -fluoro- and α, α -difluoro-acetates with dialkyl phenylphosphonites leads to the formation of unusual products including a fluorophosphinate. The reaction of ethyl bromofluoracetate with diisopropyl- and dimethyl-phenylphosphonites furnishes a complex mixture of eight and five compounds respectively. Five different compounds are obtained when ethyl bromodifluoroacetate is reacted with diisopropyl phenylphosphonite. Dimethyl phenylphosphonite yields three compounds when heated with bromochloromethane. The probable mechanism of formation of the compounds and their mass spectral characterization using GC-MS, tandem MS-MS and DART™ techniques are presented in this paper.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426500801968110