Anomalous reaction of ethyl bromofluoro- and difluoro-acetates with dialkylphosphonites

H. D. Durst, D. K. Rohrbaugh, Philip B. Smith, J. M. Nilles, T. Connell, J. A. Laramee, S. Munavalli

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2655-2668
Number of pages14
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume183
Issue number11
DOIs
StatePublished - Nov 1 2008

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Complex Mixtures
Acetates
bromochloromethane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Durst, H. D. ; Rohrbaugh, D. K. ; Smith, Philip B. ; Nilles, J. M. ; Connell, T. ; Laramee, J. A. ; Munavalli, S. / Anomalous reaction of ethyl bromofluoro- and difluoro-acetates with dialkylphosphonites. In: Phosphorus, Sulfur and Silicon and the Related Elements. 2008 ; Vol. 183, No. 11. pp. 2655-2668.
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Anomalous reaction of ethyl bromofluoro- and difluoro-acetates with dialkylphosphonites. / Durst, H. D.; Rohrbaugh, D. K.; Smith, Philip B.; Nilles, J. M.; Connell, T.; Laramee, J. A.; Munavalli, S.

In: Phosphorus, Sulfur and Silicon and the Related Elements, Vol. 183, No. 11, 01.11.2008, p. 2655-2668.

Research output: Contribution to journalArticle

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T1 - Anomalous reaction of ethyl bromofluoro- and difluoro-acetates with dialkylphosphonites

AU - Durst, H. D.

AU - Rohrbaugh, D. K.

AU - Smith, Philip B.

AU - Nilles, J. M.

AU - Connell, T.

AU - Laramee, J. A.

AU - Munavalli, S.

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AB - 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.

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