CYANOMETHYLENETRIBUTYLPHOSPHORANE

Uses

(Tributylphosphoranylidene)acetonitrile can be utilized as a reagent in the:

• Stereoselective synthesis of skytanthine and other O- and N-containing heterocycles by Mitsunobu intramolecular cycloalkylation.
• Wittig olefination of esters, lactones, N-Boc lactam, and cyclic imide to corresponding Wittig products.

General Description

(Tributylphosphoranylidene)acetonitrile is a stabilized trialkylphosphorane that can act as a substitute to the diethyl azodicarboxylate and triphenylphosphine (DEAD-TPP) system for Mitsunobu reaction between nucleophiles (HA) and alcohols (ROH) to form RA. It is highly useful when the pKa of the nucleophiles are higher than 11.