Exploring the reaction of iodine with α-diazo esters.

In this paper we describe the unprecedented reaction between α-diazo esters 1 and iodine. The reaction, carried out in the presence of aqueous NaHCO3, afforded the Z-isomer of the corresponding unsaturated-2-iodo ester 8. The configuration of compounds 8 was determined using the 3JC&bond;H coupling between carbonyl carbon atom and alkene proton. Mechanistic considerations accounting for the observed phenomena and including quantum chemical calculations are proposed. Copyright © 2008 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]