The Preparation of Deuterated Organic Compounds from Activated Organic Halides by Reduction with Zinc-Deuterium Oxide

Larry S. Trzupek, Erwin R. Stedronsky, George M. Whitesides

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11 Scopus citations

Abstract

Reductive elimination of halogen from α-halo esters with zinc and deuterium oxide in polar aprotic solvents provides a convenient method for the preparation of the corresponding α-deuterated substances. The procedures developed for carrying out these transformations can be applied to the synthesis of large quantities of either mono- or dideuterated esters with good isotopic purity. Several isolated experiments suggest that this method should also be applicable to the conversion of α-halogenated nitriles and amides to the corresponding α-deuterated materials; when applied to the reductive deuteration of α-halogenated ketones and acid chlorides, the isotopic purities of the deuterated products are lower. This technique for the synthesis of α-deuterated esters is superior to the base-catalyzed exchange techniques in general use when the prerequisite α-halogenated analogs are available, both in its economical use of deuterium oxide and in its ability to introduce a single deuterium atom into a methyl or methylene group containing multiple equivalent exchangeable protons.

Original languageEnglish (US)
Pages (from-to)3300-3303
Number of pages4
JournalJournal of Organic Chemistry
Volume37
Issue number21
DOIs
StatePublished - Oct 1 1972

ASJC Scopus subject areas

  • Organic Chemistry

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