The Chemistry of Some Isopolar Analogues of Phosphoric and Pyrophosphoric Acids |
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Authors: | G Michael Blackburn Andrew S Cumming Graham E Taylor |
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Institution: | Department of Chemistry , University of Sheffield , Sheffield , S3 7HF , U.K |
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Abstract: | Abstract We have previously established that the α-fluorination of alkanephosphonates provides analogues of phosphate esters which have improved ‘isopolarity’ relative to simple alkanephosphonates.1 This property is manifest, inter alia, in enhanced acidity and in the upfield shift for the 31P n.m.r. resonance. Indeed, for a range of halomethanephosphonic acids we have found the relationship “δP=9.61 (pKa2 - 4.59) ppm” gives an excellent correlation between these parameters. In this context, the properties of CF2CIPO(OR)2 species, derived from the Michaelis-Becker reaction of dialkyl phosphonates with Freon 22, CF2Cl2, will be described. |
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