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1,3-dihydroxybenzene-2-13C: Its preparation and reaction with chlorine and bromine in aqueous solution

✍ Scribed by Scott D. Boyce; Aldos C. Barefoot; James F. Hornig

Publisher
John Wiley and Sons
Year
1983
Tongue
French
Weight
529 KB
Volume
20
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

1,3‐cyclohexanedione‐2‐^13^C was prepared by intramolecular Claisen condensation of methyl 5‐oxohexanote‐6‐^13^C with sodium methoxide. Formation of the ketoester starting material involved treatment of a mixed dicarboxylic anhydride with an isotopicallylabelled Grignard reagent, methyl‐^13^C magnesium iodide. Dehydrogenation of carbon‐13 labelled cyclohexanedione over a palladium/carbon catalyst produced 1,3‐dihydroxybenzene‐2‐^13^C. Chlorination and bromination of dihydroxybenzene in aqueous solution yielded isotopically‐labelled chloroform and bromoform, each having enriched carbon‐13 contents equivalent to that of the organic substrate.

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