FURTHER INVESTIGATION ON IODOCYCLIZATION OF UNSATURATED PHOSPHONATES AND CARBOXYLIC COMPOUNDS

Abstract

Six δ,γ-unsaturated compounds (1a–6a) were synthesized and treated with two equivalents of iodine. It was found that the α-carboxylic group and the α-phosphoryl group could act as stabilization groups to the positive ion intermediates in the iodocyclization reaction. The mechanism of this neighbouring groups' effect is discussed.

Key Words:

• Iodocyclization
• α-phosphoryl group stabilized intermediates
• α-carboxylic group stabilized phosphonium ion intermediates unsaturated phosphonates.