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

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, Mohamed Makha.

Journal Name: Combinatorial Chemistry & High Throughput Screening

Volume 14 , Issue 1 , 2011

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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

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Article Details

VOLUME: 14
ISSUE: 1
Year: 2011
Page: [2 - 8]
Pages: 7
DOI: 10.2174/1386207311107010002

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