References
- Field , E. K. 1952 . J. Am. Chem. Soc. , 74 : 1528 The phosphonates reported here were synthesized using a modification of the method described by
- Montero , J.-L. , Clavel , J.-L. and Imbach , J.-L. 1987 . Tet. Lett. , 28 : 1163
- Worms , K. H. and Schmidt-Dunker , M. 1976 . Organic Phosphorus Compounds , 7 : 6
- McKenna , C. E. , Higa , M. T. , Cheung , N. H. and McKenna , M.-C. 1977 . Ter. Lett. , 155
- Dhawan , B. and Redmore , D. 1987 . Phosphorus and Sulfur , 32 : 119
- Avila , L. Z. , Loo , S. H. and Frost , J. W. 1987 . J. Am. Chem. Soc. , 109 : 6758
- Cordeiro , M. L. , Pompliano , D. L. and Frost , J. W. 1986 . J. Am. Chem. Soc. , 108 : 332
- Sidwell , R. W. and Huffman , J. H. 1971 . Appl. Microbiol. , 22 : 797
- The order of addition of the reactants, i.e. the addition of the aldehyde to the phosphite/amine rather than the addition of the amine to a phosphite/aldehyde mixture, must be maintained in order to minimize the number of side-products produced in the reaction. It should also be noted that the addition of the aldehyde can often be accompanied by a rapid rise in the temperature of the reactant mixture as a result of the exothermicity of the reaction to form the 1- aminoalkylphosphonate. Care should therefore be taken during this addition
- During this warmup and the subsequent period of stirring, the reaction mixture may experience a rise in temperature as the reaction proceeds. This temperature rise does not appear to decrease the yield of the reaction and recent experimental data indicate that additional heating may increase the yield in some cases
- Moedritzer , K. , ed. 1967 . Topics in Phorus Chemistry Vol. 5 , 227 However no synthetic details nor other physical data have been published, Compound has had 31P NMR data reported as a private communication by
- This compound has been previously reported by Fields (vide supra), however only limited physical data were reported (B.p. and elemental analysis)
- These compounds were characterized as mixtures as the pure compound could not be isolated from the reaction mixture. Data from work in progress suggest that the other products in the reaction mixture are the result of ester hydrolysis side-reactions. This side-reaction most likely appears with 10–12, because of the increased exposure time of the phosphonate to HCI, a result of increased solubility of these particular phosphonates as compared to their dimethyl counterparts
- Gorenstein , D. G. 1984 . Phosphorus-31 NMR , New York, NY : Academic Press .
- Gorenstein , D. G. 1975 . J. Am. Chem. Soc. , 97 : 898
- Quin , L. 1987 . Methods in Stereochemical Analysis: Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis Vol. 8 , 391
- Quin , L. J. Am. Chem. Soc. , 399
- Kaushik , M. P. , Charandabi , M. D. R. and Morse , K. W. Manuscript in preparation
- Berlin , K. D. , Claunch , R. T. and Gaudy , E. T. 1968 . J. Org. Chem. , 53 : 3090
- The Influenza A virus tests were standardized with respect to the activity of Ribaviran (1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide). The tests using Type 1 Herpes were standardized with respect to the activity of Vidarabine (1-β-D-arabinofuranosyladenine)