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Loss of Isotope Labeling in the Conversion of [ 18 O 2 ]Benzoic Acid into [ 18 O]Benzoyl Chloride with Oxalyl Chloride
Author(s) -
Haiss Peter,
Zeller KlausPeter
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200390101
Subject(s) - benzoic acid , oxalyl chloride , benzoyl chloride , chemistry , chloride , trioxane , medicinal chemistry , organic chemistry , copolymer , polymer
Tell me where the 18 O atoms are, where are they to be found? This question was raised when a large amount of the 18 O labeling was lost in the course of the conversion of [ 18 O 2 ]benzoic acid into [ 18 O]benzoyl chloride with oxalyl chloride. That the 13 C marking in [carboxy‐ 13 C]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.