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

✍ Scribed by A. A. Tolmachev; A. I. Konovets; A. N. Kostyuk; A. N. Chernega; A. M. Pinchuk

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 229 KB
Volume: 9
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(1998)9:1<41::aid-hc5>3.0.co;2-5

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✦ Synopsis

The chlorination of 5-alkoxypyrazoles containing bis-(dialkylamino)-or diphenylphosphino groups at the 4-position afforded highly unstable chlorophosphonium chlorides that dealkylated giving chlorobis(dialkylamino)-and chlorodiphenylphosphonium(3methyl-5-oxo-1-phenyl-5H-pyrazol-4-yl)ides. The Pchloro ylides do not react with aromatic aldehydes, but chlorine atoms are easily substituted with OH, NH 2

ArNH, and Et 2 N residues. They also exhibit basic properties and add hydrogen chloride with protonation at N-2.

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