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

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

Volume: 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

Affiliation:

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

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).

Cite this article as:

Rostami Charati Faramarz, Taher Maghsoodlou Malek, Mostafa Habibi-Khorassani Sayyed, Hazeri Nourallah, Ebrahimi Ali, Hossaini Zinatossadat, Ebrahimi Pouneh, Maleki Nariman, Reza Adhamdoust Sayyed, Vasheghani-Farahani Fatemeh, Marandi Ghasem, Sobolev Alexandre and Makha Mohamed, Efficient Synthesis of Stable Phosphonate Ylides and Phosphonate Esters: Reaction Between Activated Acetylenes and Triphenylphosphite in the Presence of Sulfonamide and Heterocyclic NH-Acids, Combinatorial Chemistry & High Throughput Screening 2011; 14 (1) . https://dx.doi.org/10.2174/1386207311107010002