4,5-Dihydro-1,2,3-oxadiazole: A Very Elusive Key Intermediate in Various Important Chemical Transformations

Klaus Banert, Neeraj Singh, Benjamin Fiedler, Joachim Friedrich, Marcus Korb, Heinrich Lang

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Abstract

4,5-Dihydro-1,2,3-oxadiazoles are postulated to be key intermediates in the industrial synthesis of ketones from alkenes, in the alkylation of DNA in vivo, and in the decomposition of N-nitrosoureas; they are also a subject of great interest for theoretical chemists. In the presented report, the formation of 4,5-dihydro-1,2,3-oxadiazole and the subsequent decay into secondary products have been studied by NMR monitoring analysis. The elusive properties evading characterization have now been confirmed by H-1, C-13, and N-15 NMR spectroscopy, and relevant 2D experiments at very low temperatures. Our experiments with suitably substituted N-nitrosoureas using thallium(I) alkoxides as bases under apolar conditions answer important questions on the existence and the secondary products of 4,5-dihydro-1,2,3-oxadiazole.

Original languageEnglish
Pages (from-to)15092-+
Number of pages8
JournalCHEMISTRY-A EUROPEAN JOURNAL
Volume21
Issue number43
DOIs
Publication statusPublished - 19 Oct 2015
Externally publishedYes

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