Reactions that break open bridged molecules can preserve stereochemistry
المؤلف:
Jonathan Clayden , Nick Greeves , Stuart Warren
المصدر:
ORGANIC CHEMISTRY
الجزء والصفحة:
841
2025-07-19
329
Reactions that break open bridged molecules can preserve stereochemistry
Some powerful oxidizing agents are able to cleave C–C bonds. Oxidation of camphor with concentrated nitric acid cleaves a C–C bond adjacent to the C=O group and produces a diacid known as camphoric acid. The usual reagent is nitric acid (HNO3) and oxidation goes via camphor’s enol.
Because the bridge holds the molecule in a fixed conformation, the cleaved diacid has to have a specifi c stereochemistry. There is no change at the stereogenic centres, so the reaction must give retention of configuration. We can confidently write the structure of camphoric acid with cis-CO2H groups, but any doubt is dispelled by the ability of camphoric acid to form a bridged bicyclic anhydride.
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