Microwave Induced Stereoselective Conversion of Dialkyl 2-(imido-N-yl)-3- (triphenylstibanylidene)succinates to Electron-poor (Z)-N-vinylimides
Ali Ramazani*, Ebrahim Ahmadi† and Nader Noshiranzadeh

Chemistry Department, Zanjan University, P.O. Box 45195-313, Zanjan, Iran
E-mail: a-ramazani@mail.znu.ac.ir, aliramazani@yahoo.com


Protonation of the highly reactive 1 : 1 intermediates, produced in the reaction between triphenylstibine and dialkyl acetylenedicarboxylates, by imides (phthalimide and succinimide) leads to vinyltriphenylstibinium salts, which undergo Michael addition reaction with conjugate base to produce dialkyl 2-(imido - N-yl)-3-(triphenylstibanylidene)succinates. Microwave irradiation was found to catalyze stereoselective conversion of dialkyl 2-(imido-N-yl)-3-(triphenylstibanylidene)succinates to electron-poor (Z)-N-vinylimides in the presence of silica gel in solvent-free conditions at microwave power 0.3 kW in 3 min in high conversions.

Microwave irradiation, Stibine ylide, Silica gel, (Z)-N-Vinylimide.
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  • Asian J. Chem. /
  •  2006 /
  •  18(1) /
  •  pp 125-128