Facile Phosphite to Phosphonate Rearrangement of a Trialkanolamine-derived Triphosphite Promoted by Triethylaluminum¹

Abstract

A facile room temperature rearrangement of a trialkanolamine-derived triphosphite, 1 , to the monophosphonate 5 promoted by three equivalents of triethylaluminum is described. The diphosphonate 6 was prepared by the addition of three equivalents of triethylaluminum to the monophosphonate 5 . A mechanism is suggested involving a transition state or intermediate with coordination of the trialkylaluminum to the migrating oxygen.

Keywords:

• Aluminum-phosphorus interaction
• Michaelis-Arbusov reaction
• P─C bond formation
• phosphonate
• Phosphite Rearrangement
• trialkylaluminum
• triethylaluminum

Acknowledgments

The authors wish to thank Ciba Specialty Chemicals Corp. for support and permission to publish this work. The authors thank Mrs. L. Burke for acquiring NMR spectral data; Mr. B. Piatek for MS; and Mr. M. Nirsberger for obtaining IR spectra