SYNTHESIS OF HIGHLY ELECTRON-POOR ALKENES FROM IN SITU GENERATED STABILIZED PHOSPHORUS YLIDES AND NINHYDRIN VIA INTERMOLECULAR WITTIG REACTION

Abstract

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

Keywords:

• Acetylenic ester
• alcohol
• intermolecular Wittig reaction
• ninhydrin
• triphenylphosphine

The Zanjan University Research Council supported this work.