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Non-conventional Behavior of a 2,1-Benzazaphosphole: Heterodiene or Hidden Phosphinidene?

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F21%3A39918130" target="_blank" >RIV/00216275:25310/21:39918130 - isvavai.cz</a>

  • Result on the web

    <a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202101686" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202101686</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/chem.202101686" target="_blank" >10.1002/chem.202101686</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Non-conventional Behavior of a 2,1-Benzazaphosphole: Heterodiene or Hidden Phosphinidene?

  • Original language description

    The titled 2,1-benzazaphosphole (1) (i. e. ArP, where Ar=2-(DippN=CH)C6H4, Dipp=2,6-iPr(2)C(6)H(3)) showed a spectacular reactivity behaving both as a reactive heterodiene in hetero-Diels-Alder (DA) reactions or as a hidden phosphinidene in the coordination toward selected transition metals (TMs). Thus, 1 reacts with electron-deficient alkynes RC equivalent to CR (R=CO2Me, C5F4N) giving 1-phospha-1,4-dihydro-iminonaphthalenes 2 and 3, that undergo hydrogen migration producing 1-phosphanaphthalenes 4 and 5. Compound 1 is also able to activate the C=C double bond in selected N-alkyl/aryl-maleimides RN(C(O)CH)(2) (R=Me, tBu, Ph) resulting in the addition products 7-9 with bridged bicyclic [2.2.1] structures. The binding of the maleimides to 1 is semi-reversible upon heating. By contrast, when 1 was treated with selected TM complexes, it serves as a 4e donor bridging two TMs thus producing complexes [mu-ArP(AuCl)(2)] (10), [(mu-ArP)(4)Ag-4][X](4) (X=BF4 (11), OTf (12)) and [mu-ArP(Co-2(CO)(6))] (13). The structure and electron distribution of the starting material 1 as well as of other compounds were also studied from the theoretical point of view.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10402 - Inorganic and nuclear chemistry

Result continuities

  • Project

    <a href="/en/project/GA18-10222S" target="_blank" >GA18-10222S: From simple precursors to unprecedented heterocyclic systems containing heavier Group 15 elements</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2021

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Chemistry - A European Journal

  • ISSN

    0947-6539

  • e-ISSN

  • Volume of the periodical

    27

  • Issue of the periodical within the volume

    52

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    13

  • Pages from-to

    13149-13160

  • UT code for WoS article

    000670513500001

  • EID of the result in the Scopus database

    2-s2.0-85109622617