Issue 10, 1999

The reaction of diphenyl and dialkyl phosphorochloridates with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Formation of phosphonate diesters via N→C phosphorus migration

Abstract

Diphenyl and neopentylene phosphorochloridates react with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in acetonitrile to form amidine adducts 3 or 10. These undergo further conversion into the corresponding alkene aminals, followed by probable N→C phosphorus migration to produce stable 6-substituted phosphinoyl derivatives of DBU, 6 or 12, respectively. Diethyl phosphorohalidates (chloride and bromide) also form amidine adduct 13 with DBU, but this does not undergo N→C phosphorus migration.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1999, 2071-2075

The reaction of diphenyl and dialkyl phosphorochloridates with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Formation of phosphonate diesters via N→C phosphorus migration

A. Kers, I. Kers and J. Stawinski, J. Chem. Soc., Perkin Trans. 2, 1999, 2071 DOI: 10.1039/A904502C

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