Iodinolysis of boronic acids

Abstract

The relative rates of iodinolysis of benzene-, thiophen-2-, and thiophen-3-boronic acids at 25° were found to be 1 : 700 : 10⁴, or for thiophen-2- and thiophen-3-boronic acid 14 : 1. These values correlate reasonably well with data on protodetrimethylsilylation, and may be satisfactorily understood in terms of current molecular orbital theory. It does not, however, appear to be possible to offer a. simple electronic interpretation of the relative acid strengths of the boronic acids.