Preparation of Bromoiodopropenoic Acids by Stereospecific Nucleophilic Substitution at Vinylic Carbon

Abstract

The bromoiodopropenoic acids (E)‐2‐bromo‐3‐iodopropenoic acid 5 and (Z)‐2‐bromo‐3‐iodopropenoic acid 6 were prepared by stereospecific nucleophilic substitution of the corresponding vinylic bromides. The structure of the (Z)‐isomer was confirmed by X‐ray crystallography.

Keywords:

• Bromoiodopropenoic acids
• stereospecific substitution
• vinylic carbon

Acknowledgments

This work was funded by the U.S. Environmental Protection Agency Contract No. 3L‐3031‐NTFA. A. J. L. thanks the National Sciences and Engineering Research Council of Canada (NSERC) and University of Toronto for funding.