Simple synthesis of (E) and (Z)-2-(arylmethylidene)-N-phenyl succinimides via Wittig olefination by using PS-TPP resin

GRAPHICAL ABSTRACT

ABSTRACT

PS-Triphenylphosphine resin has been used in the Wittig reaction to prepare (E)- and (Z)-2-(arylmethylidene)-N-phenylsuccinimides. PS-TP phosphoranylidene-N-phenylsuccinicimide has been obtained from PS-TPP and N-phenylmaleimide. The Wittig reaction of stabilized PS-TPP ylide with an aromatic aldehyde produced the (E)-alkene as the major product, isolated in high yields by simple filtration of PS-resin, from the reaction mixture. The better stabilized PS-TPP succinic anhydride does not react in the same conditions.

KEYWORDS:

• Phosphorus ylides
• PS-TPP
• Wittig olefination
• TPPSA