REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .11. RING-OPENING REACTIONS OF ALIPHATIC MONOFUNCTIONALIZED AND DIFUNCTIONALIZED CIS AND TRANS 2,3-EPOXY AND 3,4-EPOXY ESTERS

The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the azidolysis of simple aliphatic cis and trans 2,3- and 3,4-epoxy esters and in the corresponding derivatives bearing an ether functionality (OBn) in an allylic relationship to the oxirane ring. The results indicate that the behavior of these epoxides is influenced both by the opening conditions (standard or metal-assisted) and the promoting metal salt [LiClO4 or Mg(ClO4)(2)]