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view:21607   Last Update: 2019-1-30

Nader NoshiranZadeh

Ali  Ramazani;   Abbas Azizian;  Maryam Bandpey; Nader Noshiranzadeh
One-Step Synthesis of Electron-Poor Alkenes from Triphenylphosphine, Acetylenic Esters, 2,2,2-Trichloroethanol, and Ninhydrin
Abstract


Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 2,2,2- trichloroethanol leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction with a conjugate base to produce the corresponding chlorine-containing stabilized phosphorus ylides. An intermolecular Wittig reaction of the chlorine-containing stabilized phosphorus ylides with ninhydrin leads to the corresponding highly electron-poor chlorine-containing alkenes.

 

 

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