Zwitterionic phosphonium sulfonates as easily phase-separable ion-tagged Wittig reagents.
Zwitterionic phosphonium sulfonates 3, conveniently derived from TPPMS (1), can be used as Wittig reagents in solution. The excess reagents and byproduct TPPMSO (6) can be easily separated from the product alkenes by simple precipitation with a less polar solvent. The alkenes thus obtained were often sufficiently pure without chromatographic purification. A one-pot protocol for the synthesis of alpha,beta-unsaturated esters has been developed and appears to be convenient.
Huo
Congde
C
Department of Chemistry, McGill University, Montreal, Quebec, Canada H3A 2K6.
He
Xun
X
Chan
Tak Hang
TH
D000475:Alkenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D063065:Organophosphonates / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*
D000475:Alkenes; D007202:Indicators and Reagents; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D013451:Sulfonic Acids