1,5-Phosphonium betaines from N-triflylpropiolamides, triphenylphosphane, and active methylene compounds

• Main Authors: Vito A. Fiore, Chiara Freisler, Gerhard Maas
• Format: Article
• Language: English
• Published: Beilstein-Institut 2019-11-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: betaines; multi-component reactions; n-triflylamides; phospha-michael reaction; propiolamides
• Online Access: https://doi.org/10.3762/bjoc.15.253

N-Phenyl-N-(trifluoromethylsulfonyl)propiolamides react with triphenylphosphane in the presence of various active methylene compounds CH2XY in a 1:1:1 molar ratio to furnish 1-phosphonium-5-oxabetaines, Ph3P+–C(R)=CH–C(O–)=CXY. These betaines are formed preferentially, but not exclusively, as E-diastereoisomers with respect to the vinylic double bond. In some cases, separation of the two diastereoisomers was achieved by fractionating crystallization. Structure determination by X-ray diffraction analysis revealed marked conformational differences around the CH–C(O–) single bond of E and Z-isomers and extended charge delocalization in the anionic part.