Abstract
Tell me where the 18O atoms are, where are they to be found? This question was raised when a large amount of the 18O labeling was lost in the course of the conversion of [18O2]benzoic acid into [18O]benzoyl chloride with oxalyl chloride. That the 13C marking in [carboxy-13C]benzoic acid was retained fully under the same conditions made the matter even more mysterious. Equilibration with 1,3-dioxetane (see scheme) or 1,3,5-trioxane intermediates can explain the oxygen-atom exchange with retention of identity of the carbon atom of the carbonyl group.
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