In 1960, Thompson et al. (I) reported a technique for structural analysis in which organic compounds were volatilized at temperatures of 150-350 °C in a stream of hydrogen and passed over a hydrogenation catalyst. Multiple bonds were saturated and functional groups were removed so that a saturated hydrocarbon was produced with the original carbon skeleton intact except that with some functional groups, the connected carbon atom was also removed. Beroza et al. ( 2) then developed a catalyst tube which was connected to a gas chromatograph and allowed hydrogenolysis and detection of the product in one step.Our interest in this technique arose from our need to determine whether natural products containing a furan ring were 2-alkyl or 2,5-dialkyl substituted. Since furan derivatives suitable for testing are not commercially available, we synthesized two such compounds and determined their hydrogenolysis products.
EXPERIMENTALHydrogenolysis was conducted with the National Instrument Laboratories Beroza Carbon Skeleton Determinator. The catalyst was neutral 1 % Pd on Gas-Chrom P and the hydrogenolysis temperature was 260 °C.
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