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Efficient Synthesis of Stable Phosphonate Ylides and Phosphonate Esters: Reaction Between Activated Acetylenes and Triphenylphosphite in the Presence of Sulfonamide and Heterocyclic NH-Acids

[ Vol. 14 , Issue. 1 ]

Author(s):

Faramarz Rostami Charati, Malek Taher Maghsoodlou, Sayyed Mostafa Habibi-Khorassani, Nourallah Hazeri, Ali Ebrahimi, Zinatossadat Hossaini, Pouneh Ebrahimi, Nariman Maleki, Sayyed Reza Adhamdoust, Fatemeh Vasheghani-Farahani, Ghasem Marandi, Alexandre Sobolev and Mohamed Makha   Pages 2 - 8 ( 7 )

Abstract:


An efficient synthesis of stable phosphonate ylides and phosphonate esters is described via a one-pot reaction between activated acetylenes and triphenylphosphite in the presence of sulfonamides and heterocyclic NH-acids. Single X-ray diffraction analysis and NMR studies were used in characterizing the ylides and phosphonate ester products. Dynamic NMR studies performed on a phosphonate ylide allowed the calculation of the free energy barrier for the interconversion between the geometrical isomers (E) and (Z).

Keywords:

Dialkyl acetylenedicarboxylates, sulfonamide NH-acids, heterocyclic NH-acids, triphenylphosphite, phosphonate ylide, dynamic NMR, IR, C NMR spectra, single crystal X-ray diffraction analysis, Heraeus CHN-O-Rapid analyzer, FINNIGAN-MATT, Shimadzu IR-460 spectrometer, BRUKER DRX-500 AVANCE, Oxford Diffraction Xcalibur-S CCD, X-Ray Crystallography, SHELX-97, 2-benzoxazolinone

Affiliation:

Faculty of Basic Science, Gonbad Institutes of Higher Education, P.O. Box 163, Gonbad, Iran.



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