Stable phosphorus ylides and heterocyclic phosphonate esters derivatives synthesised from stereoselective reactions between triphenyl phosphite and activated acetylenic esters

2008 ◽  
Vol 2008 (2) ◽  
pp. 79-82 ◽  
Author(s):  
Malek Taher Maghsoodlou ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Mahmoud Nassiri ◽  
Sayyed Reza Adhamdoust ◽  
Jaber Salehzadeh
Keyword(s):  
Triphenyl Phosphite ◽  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
Stereoselective Reactions ◽  
Phosphonate Esters ◽  
Stable Phosphorus Ylides

Synthesis and dynamic 1H NMR study of stable phosphorus ylides derived from reaction between heterocyclic NH-acids and triphenylphosphine in the presence of acetylenic esters

2006 ◽  
Vol 2006 (4) ◽  
pp. 215-217 ◽  
Author(s):  
Nourollah Hazeri ◽  
Sayyed M. H. Khorassani ◽  
Malek T. Maghsoodlou ◽  
Ghasem Marandi ◽  
Mahmoud Nassiri ◽  
...  
Keyword(s):  
1H Nmr ◽  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
Nmr Study ◽  
Dynamic 1H Nmr ◽  
Stable Phosphorus Ylides

scholarly journals A simple synthesis of stable phosphorus ylides from reaction between triphenylphosphine and acetylenic esters in the presence of CH-acid compounds

ARKIVOC ◽  
2008 ◽  
Vol 2008 (13) ◽  
pp. 218-227 ◽  
Author(s):  
Malek Taher Maghsoodlou ◽  
Hamid Reza Shaterian ◽  
Ghasem Marandi ◽  
Fahimeh Shahraki Poor ◽  
Jaber Salehzadeh
Keyword(s):  
Simple Synthesis ◽  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
Stable Phosphorus Ylides

Chemoselective Synthesis of New Stable Phosphorus Ylides from the Reaction Between Triphenylphosphine and Activated Acetylenic Esters in the Presence of Heterocyclic Biological Bases

2010 ◽  
Vol 186 (1) ◽  
pp. 21-30 ◽  
Author(s):  
Sayyed Mostafa Habibi-Khorassani ◽  
Malek Taher Maghsoodlou ◽  
Nourallah Hazeri ◽  
Khatereh Bagherpour ◽  
Mohsen Rostamizadeh ◽  
...  
Keyword(s):  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
Chemoselective Synthesis ◽  
Stable Phosphorus Ylides

Theoretical Study, An Efficient Synthesis Route to, and Kinetic Investigation of, Stable Phosphorus Ylides Derived from Benzamide

2009 ◽  
Vol 34 (3) ◽  
pp. 261-288 ◽  
Author(s):  
Sayyed Mostafa Habibi-Khorassani ◽  
Ali Ebrahimi ◽  
Malek Taher Maghsoodlou ◽  
Hamideh Saravani ◽  
Mohammad Zakarianezhad ◽  
...  
Keyword(s):  
Theoretical Study ◽  
Theoretical Calculations ◽  
Condensation Reaction ◽  
Kinetic Investigation ◽  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
One Pot ◽  
Rate Determining Step ◽  
Mechanistic Investigation ◽  
Stable Phosphorus Ylides

The synthesis, theoretical study and a kinetics and mechanistic investigation are described as a one-pot condensation reaction between benzamide and acetylenic esters in the presence of triphenyphosphine to generate a novel stable phosphorus ylides. For the first time, theoretical calculations have been employed to assign the most stable isomers ( Z or E) of phosphorus ylides 4a-c by AIM and NBO theory, in which Z-4(a,b) are the more stable forms, whereas Z-4c appears as a single isomer. In these cases, the 1H, 13C and 31P NMR spectra of these ylides are consistent with the results obtained from theoretical calculations. Kinetic investigation of the new ylides was undertaken by UV. Useful information was obtained from studies of the effect of solvent, structure of reactants (different alkyl groups within the acetylenic esters), and also the concentration of reactants on the rate of reactions. The proposed mechanism was consistent with the results obtained; from the steady-state approximation, the first step ( k2) of the reaction was recognized as the rate-determining step on the basis of the experimental data.

Water–acetone Media Enforced Chemoselective Synthesis of 2-substituted Pyrrole Stable Phosphorus Ylides from Reaction between Pyrrole and Acetylenic Esters in the Presence of Triphenylphosphine

2007 ◽  
Vol 2007 (10) ◽  
pp. 566-568 ◽  
Author(s):  
Malek Taher Maghsoodlou ◽  
Nourollah Hazeri ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Zohreh Moeeni ◽  
Ghasem Marandi ◽  
...  
Keyword(s):  
Good Yield ◽  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
Dialkyl Acetylenedicarboxylates ◽  
Chemoselective Synthesis ◽  
Stable Phosphorus Ylides

Pyrrole undergoes a smooth reaction with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine in a mixture of water–acetone (50:50) as a solvent pathway to produce phosphorus ylides of 2-substituted pyrrole in good yield.

Chemoselective synthesis of phosphorus ylides through the reaction of 2-mercaptobenzimidazole and 2-hydroxybenzimidazole with triphenylphosphine and acetylenic esters

2006 ◽  
Vol 27 (4) ◽  
pp. 341-346 ◽  
Author(s):  
Malek T. Maghsoodlou ◽  
Reza Heydari ◽  
S. Mostafa Habibi Khorassani ◽  
Mohammad K. Rofouei ◽  
Mahmoud Nassiri ◽  
...  
Keyword(s):  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
Chemoselective Synthesis
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