Iodinolysis of boronic acids

descriptionPublicationkeyboard_double_arrow_right Article 01 Oct 1965 English Publisher:CSIRO PublishingJournal:Australian Journal of Chemistry, volume 18, pages 1,527-1,538 (issn: 0004-9425, eissn: 1445-0038,

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Authors: RD Brown; AS Buchanan; AA Humffray;

doi: 10.1071/ch9651527

Iodinolysis of boronic acids

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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.

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