References
- DeBruin , K. E. and Boros , E. E. 1989 . Tetrahedron Lett. , 30 : 1047
- The procedure is a modification of that used3 to react phosphoramidates with acid chlorides. A THF solution of the phosphorus amide was added dropwise to a stirred suspension of sodium hydride in THF and the resulting mixture was heated for two hours. After cooling to 0°C, a THF solution of the acid chloride was added and the mixture was stirred for 15 min and quenched with water. Ia, Ib, Id, and le were oils and were purified by chromatography on Silica Gel using a 3/1 volume ratio of dichloromethane/ethyl acetate as eluent. Ic, a solid, was recrystallized from carbon tetrachloride (mp 123–126°C with decomposition).
- Hendrickse , T. F. , Mizrahi , V. and Modro , T. A. 1984 . Phosphorus and Sulfur , 20 : 93
- Hudson , R. F. 1965 . Structure and Mechanism in Organo-phosphorus Chemistry , 68 New York, N.Y. : Academic Press .
- The carbonyl stretching frequency for Ie indicates a particularly strong C˭O bond (Table I).
- Kirby , A. J. and Warren , S. G. 1967 . The Organic Chemistry of Phosphorus , 314 – 317 . New York, N.Y. : Elsevier . K. E. DeBruin and C. E. Ebersole, unpublished results. For alkyl systems, see: