Preparation of (cyanomethylene)trimethylphosphorane as a new Mitsunobu-type reagent.
(Cyanomethylene)trimethylphosphorane (CMMP) mediates Mitsunobu-type reactions, which are a versatile method for the alkylation of various nucleophiles (HA) with alcohols (ROH) to give RA. CMMP is quite effective for the reaction of carbon nucleophiles whose pK(a) value are higher than 13. CMMP, which is very sensitive to air and moisture, was synthesized in two steps starting from chloroacetonitrile.
Sakamoto
Izumi
I
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Kaku
Hiroto
H
Tsunoda
Tetsuto
T
D000478:Alkylation; D000607:Aminoacetonitrile / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010755:Organophosphates / Q000138:chemical synthesis*; D010753:Phosphoranes / Q000138:chemical synthesis*; D013678:Technology, Pharmaceutical / Q000295:instrumentation / Q000379:methods*
D007202:Indicators and Reagents; D010755:Organophosphates; D010753:Phosphoranes; D000607:Aminoacetonitrile; C003715:trimethyl phosphate