Synthesis of 4-(N,N-Dialkylamino)benzyltriphenylphosphonium Iodides from Hydroxymethyltriphenylphosphonium Iodide and N,N-Dialkylaniline

Abstract

Reinvestigation of the one-pot synthesis of 4-(N,N-dialkylamino)benzyltriphenylphosphonium iodides has shown that the product forms after the initial condensation of triphenylphosphine upon formaldehyde.

Keywords:

• Formaldehyde
• N,N-dialkylaniline
• triphenylphosphine
• Wittig

ACKNOWLEDGMENTS

The financial support from the Office of Naval Research in gratefully acknowledged. Thanks to Andrew P. Chafin (NAWCWD) for comments and suggestions about the manuscript. Thanks to Dr. Robert D. Chapman (NAWCWD) for the generous loan of the inverse Dean–Stark trap. Thanks to Drs. Brian Zentner and Hung Hoang (both of NAWCWD) for supplying the triphenylphosphine.