Dealkylation of 4-phosphorylated 5-alkoxypyrazoles: Easy synthetic access to P-chloro ylides

Abstract

The chlorination of 5-alkoxypyrazoles containing bis-(dialkylamino)- or diphenylphosphino groups at the4-position afforded highly unstable chlorophosphoni-um chlorides that dealkylated giving chlorobis(di-alkylamino)- and chlorodiphenylphosphonium(3-methyl-5-oxo-1-phenyl-5H-pyrazol-4-yl)ides. The P-chloro ylides do not react with aromatic aldehydes, but chlorine atoms are easily substituted with OH, NH2 ArNH, and Et2N residues. They also exhibit basic properties and add hydrogen chloride with protonation at N-2. © 1998 John Wiley & Sons, Inc. Heteroatom Chem 9:41–49, 1998