092ChemInform Abstract A series of eleven 1-chloroethyl carbonates such as (III), prepared by reaction of the chloroformate (I) with the alcohols (II), is converted into the corresponding fluoroformates (IV) by treatment with KF in the presence of a crown ether and under reduced pressure.
another 10 min, and the excess palladium(II) precipitated as Pd(0) by reaction with Zn powder. The reaction mixture was then cooled to ~2 °C. A (2,4-dinitrophenyl)hydrazine solution was prepared as previously described and also cooled to 2 °C. To this solution was added the cooled reaction mixture. The solids were collected and washed with water to remove any excess hydrazine reagent. After air drying the 2,4-DNP's were dissolved in hot benzene and filtered, and the extract was cooled to crystallize the 2,4-DNP's, which were then collected, dried, and dissolved in CDC13 for NMR analysis to determine total product distribution by NMR peak integration. Fortunately each product possessed a proton whose chemical shift was different from all other protons in the reaction mixture. For example in the oxidation of crotyl alcohol the crotonaldehyde vinylic protons at 6.3 ppm, the Hb protons of 8 at 4.2 ppm, the Hc protons of 13 at 4.6 ppm, and the H" protons of 11 at 3.9 ppm were used for this purpose. The individual 2.4-DNP's of the products were separated by column chroma-
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