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Synthesis 2006(18): 3019-3024
DOI: 10.1055/s-2006-950200
DOI: 10.1055/s-2006-950200
PAPER
© Georg Thieme Verlag Stuttgart · New York
The Preparation of Dialkyl 1-Hydroxyalkylphosphonates in the Reaction of Trialkyl Phosphites with Oxonium Salts Derived from Aldehydes or Ketones
Weitere Informationen
Received
16 March 2006
Publikationsdatum:
15. August 2006 (online)
Publikationsverlauf
Publikationsdatum:
15. August 2006 (online)
Abstract
The reaction of trialkyl phosphites with aldehydes or ketones in the presence of hydrogen chloride gives dialkyl 1-hydroxyalkylphosphonates via Arbusov-like reaction of oxonium salts derived from aldehydes or ketones. This reaction is a very convenient instant method for the preparation of dialkyl 1-hydroxyalkylphosphonates with a good yield as an alternative to the well-known Abramov reaction.
Key words
Abramov reaction - nucleophilic addition - addition reactions - 1-hydroxyphosphonates
- The chemistry of 1-hydroxyalkylphosphonic acids is of course much older. 1-Hydroxyalkylphosphonic acids were prepared in the 19th and 20th centuries by Marie and Fossek:
-
2a
Marie C. C. R. Hebd. Seances Acad. Sci. 1902, 135: 107 -
2b
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Fossek W. Monatsh. Chem. 1886, 5: 627 -
2f
Fossek W. Monatsh. Chem. 1886, 7: 20 - Later, Conant described the preparation of some 1-hydroxyalkylphosphonic acids in the reaction of phosphorous (phosphonic) acid or phosphorus trichloride with aldehydes or ketones:
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2g
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Conant JB. J. Am. Chem. Soc. 1921, 43: 1705 - This reaction is commonly called the Abramov reaction. For the most representative Abramov papers, see:
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3i
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3n
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3o
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References
Since citation of more than 500 papers in this short article is not appropriate we will send a copy of a text file with the citations to interested readers.