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

Research output: Contribution to journalArticle

1 Citation (Scopus)

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

Cite this

Banert, Klaus ; Singh, Neeraj ; Fiedler, Benjamin ; Friedrich, Joachim ; Korb, Marcus ; Lang, Heinrich. / 4,5-Dihydro-1,2,3-oxadiazole : A Very Elusive Key Intermediate in Various Important Chemical Transformations. In: CHEMISTRY-A EUROPEAN JOURNAL. 2015 ; Vol. 21, No. 43. pp. 15092-+.
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4,5-Dihydro-1,2,3-oxadiazole : A Very Elusive Key Intermediate in Various Important Chemical Transformations. / Banert, Klaus; Singh, Neeraj; Fiedler, Benjamin; Friedrich, Joachim; Korb, Marcus; Lang, Heinrich.

In: CHEMISTRY-A EUROPEAN JOURNAL, Vol. 21, No. 43, 19.10.2015, p. 15092-+.

Research output: Contribution to journalArticle

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T1 - 4,5-Dihydro-1,2,3-oxadiazole

T2 - A Very Elusive Key Intermediate in Various Important Chemical Transformations

AU - Banert, Klaus

AU - Singh, Neeraj

AU - Fiedler, Benjamin

AU - Friedrich, Joachim

AU - Korb, Marcus

AU - Lang, Heinrich

PY - 2015/10/19

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AB - 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.

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KW - AB-INITIO

KW - 1,3-DIPOLAR CYCLOADDITION

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KW - OXIDE

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