THE DEHALOGENATION OF DIHALOGENOMETHYLENEBISPHOSPHONATES
- 1 September 1984
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 21 (1) , 1-4
- https://doi.org/10.1080/03086648408073119
Abstract
Tetraesters of dihalogenomethylenebisphosphonic acids undergo nucleophilic dehalogenation with potassium fluoride or hydroxide in solution in acetonitrile in the presence of [18,6]-crown ether. Fluoride ion is the best nucleophile for dehalogenation and there is no evidence for nucleophilic displacement of halide ion by attack at the central atom of the methylenebisphosphonic esters. Conditions were developed for the monodehalogenation of tetraisopropyl dibromo- and dichloromethylenebisphosphonates in good yield.Keywords
This publication has 10 references indexed in Scilit:
- Determination of formation constants of calcium complexes of difluoromethylenediphosphonic acid and related diphosphonatesAnalytical Chemistry, 1983
- Ammonia chemical ionization mass spectra of esters and amides of oxyacids of phosphorusJournal of Mass Spectrometry, 1983
- The inhibition of the RNA polymerase activity of influenza virus A by pyrophosphate analoguesNucleic Acids Research, 1983
- Preparation of F-methylene bis phosphonatesJournal of Fluorine Chemistry, 1980
- Halomethyl—metal compoundsJournal of Organometallic Chemistry, 1973
- CHLORINE, BROMINE, IODINE AND ASTATINEPublished by Elsevier ,1973
- New approaches to the preparation of halogenated methylenediphosphonates, phosphonoacetates, and malonatesThe Journal of Organic Chemistry, 1971
- Metalated methylenediphosphonate esters. Preparation, characterization and synthetic applicationsJournal of Organometallic Chemistry, 1968
- Tetrasodium carbonyldiphosphonate. Synthesis, reactions, and spectral propertiesThe Journal of Organic Chemistry, 1967
- A Convenient Method for the Monobromination of Active Methylene CompoundsBulletin of the Chemical Society of Japan, 1964