Deuterium Isotope Effects for Intramolecular Rearrangements of Cation Radicals in Mass Spectrometers and in Solution
Armstrong, Mark W.
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Several approaches toward the synthesis of di-n-butyl-amine-4-d3 were attempted. One of them involved malonic ester. This approach was rejected because too many steps were involved, the materials were too volatile, and low yields were obtained in trial runs of the malonic ester step. A synthesis of propanol-3-d3 was also rejected because, to prevent the formation of tributylamine and tetrabutylammonium ion, a large excess of the amine is required. The synthetic approach used by Corey and Hertler was rejected because the reported yields of each step were low (<50%) and the reactions required several days each to run. The synthetic approach finally used started with the preparation of propyl bromide-3-d3 from propanol-3-d3 using phosphorus pentabromide.