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COMMUNICATION

NOVEL OBSERVATION ON BASE-CATALYZED BENZOYLATION OF DIALKYL PHOSPHORANILIDATES

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Pages 115-119 | Received 15 Jan 1986, Published online: 13 Dec 2006

References

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  • Stec , W. J. and Lopusinski , A. 1973 . Tetrahedron , 29 : 547
  • 1970 . J. Org. Chem. , 35 : 2849 The term cis refers to diequatorial positions of 4-methyl and the senior exocyclic group on phosphorus, as determined by the sequence rule, while trans refers to equatorial -axial relationship between these two groups
  • 31P NMR spectra were recorded on Jeol JNM FX-60 (24.2 MHz) instruments. Negative values were assigned for compounds absorbing upfield from 85% H3PO4
  • The reaction of diastereomeric mixture of 2-chloro-2-oxo-4-methyl-1,3,2-dioxaphosphorinanes with sodium and benzanilide led to the mixture of products absorbing in 31P NMR at -7.9 ppm, -11.8 ppm, -17.8 ppm, which proves that under applied spectroscopic conditions6 diastereomers of 4 are indistinguishable
  • Martin , G. J. , Sanches , M. and Marre , M. -R. 1983 . Tetrahedron Lett. , 24 : 4989
  • N-dialkylphosphoryl N,N'-dialkyl(aryl)-ureas and -thioureas undergo base-catalyzed transformations into corresponding carbodiimides with concomitant formation of dialkyl phosphates or phosphorothioates, respectively (M. Mikolajczyk-personal communication)
  • Chandrasegaran , S. , Murakami , A. and Kan , L. 1984 . J. Org. Chem. , 49 : 4951 W. Dabkowski, J. Michalski, Z. Skrzypczynski, Chem. Ber., 118, 1809 (1985)
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