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  Isolation and reactivity of an elusive diazoalkene

Antoni, P. W., Golz, C., Holstein, J. J., Pantazis, D. A., & Hansmann, M. M. (2021). Isolation and reactivity of an elusive diazoalkene. Nature Chemistry, 13(6), 587-593. doi:10.1038/s41557-021-00675-5.

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Antoni, P. W.1, 2, Author
Golz, C.2, Author
Holstein, J. J.1, Author
Pantazis, D. A.3, Author           
Hansmann, M. M.1, 2, Author
Affiliations:
1Fakultät für Chemie und Chemische Biologie, Technische Universität Dortmund, Dortmund, Germany, ou_persistent22              
2Georg-August Universität Göttingen, Institut für Organische und Biomolekulare Chemie, Göttingen, Germany, ou_persistent22              
3Research Group Pantazis, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541711              

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 Abstract: Most functional groups, especially those consisting of the abundant elements of organic matter—carbon, nitrogen and oxygen—have been extensively studied and only very few remain speculative due to their high intrinsic reactivity. In contrast to the well-explored chemistry of diazoalkanes (R2C=N2), diazoalkenes (R2C=C=N2) have been postulated in several organic transformations, but remain elusive long-sought intermediates. Here, we present a room-temperature stable diazoalkene, utilizing a dinitrogen transfer from nitrous oxide. This functional group shows dual-site nucleophilicity (C and N atoms) and features a bent C–C–N entity (124°) and a long N–N bond together with a remarkable low infrared absorption (1,944 cm–1). Substitution of N2 by an isocyanide leads to a vinylidene ketenimine. Furthermore, photochemically triggered loss of dinitrogen might proceed through a transient triplet vinylidene. We anticipate the existence of a stable diazoalkene functional group to pave an exciting avenue into the chemistry of low-valent carbon and unsaturated carbenes.

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Language(s): eng - English
 Dates: 2020-08-262021-03-052021-06-01
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1038/s41557-021-00675-5
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Title: Nature Chemistry
  Abbreviation : Nat. Chem.
Source Genre: Journal
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Publ. Info: London, UK : Nature Publishing Group
Pages: - Volume / Issue: 13 (6) Sequence Number: - Start / End Page: 587 - 593 Identifier: ISSN: 1755-4330
CoNE: https://pure.mpg.de/cone/journals/resource/1755-4330