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Banert K, Singh N, Fiedler B, et al. 4,5-Dihydro-1,2,3-oxadiazole: A Very Elusive Key Intermediate in Various Important Chemical Transformations. Chemistry. 2015;21(43):15092-9doi: 10.1002/chem.201502326.
Banert, K., Singh, N., Fiedler, B., Friedrich, J., Korb, M., & Lang, H. (2015). 4,5-Dihydro-1,2,3-oxadiazole: A Very Elusive Key Intermediate in Various Important Chemical Transformations. Chemistry (Weinheim an der Bergstrasse, Germany), 21(43), 15092-9. https://doi.org/10.1002/chem.201502326
Banert, Klaus, et al. "4,5-Dihydro-1,2,3-oxadiazole: A Very Elusive Key Intermediate in Various Important Chemical Transformations." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,43 (2015): 15092-9. doi: https://doi.org/10.1002/chem.201502326
Banert K, Singh N, Fiedler B, Friedrich J, Korb M, Lang H. 4,5-Dihydro-1,2,3-oxadiazole: A Very Elusive Key Intermediate in Various Important Chemical Transformations. Chemistry. 2015 Oct 19;21(43):15092-9. doi: 10.1002/chem.201502326. Epub 2015 Aug 10. PMID: 26260871.
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Chemistry. 2015 Oct 19;21(43):15092-9. doi: 10.1002/chem.201502326. Epub 2015 Aug 10.

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

Chemistry (Weinheim an der Bergstrasse, Germany)

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

Affiliations

  1. Organic Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz (Germany) https://www.tu-chemnitz.de/chemie/org/index.html.en. [email protected].
  2. Organic Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz (Germany) https://www.tu-chemnitz.de/chemie/org/index.html.en.
  3. Theoretical Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz (Germany).
  4. Theoretical Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz (Germany). [email protected].
  5. Inorganic Chemistry, Technische Universität Chemnitz, 09107 Chemnitz (Germany).

PMID: 26260871 DOI: 10.1002/chem.201502326

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 (1) H, (13) C, and (15) N 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.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: NMR spectroscopy; alkylation; cycloreversion; nucleophilic substitution; reactive intermediates

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