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Hetero Diels-Alder Reactions of Masked Dienes Containing Heavy Group 15 Elements

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F20%3A39916591" target="_blank" >RIV/00216275:25310/20:39916591 - isvavai.cz</a>

  • Result on the web

    <a href="https://doi.org/10.1002/chem.201904953" target="_blank" >https://doi.org/10.1002/chem.201904953</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/chem.201904953" target="_blank" >10.1002/chem.201904953</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Hetero Diels-Alder Reactions of Masked Dienes Containing Heavy Group 15 Elements

  • Original language description

    Treatment of N,C,N-chelated organopnictogen(I) compounds ArE (1-3) (Ar=2,6-(RN=CH)(2)C6H3, E/R=As/Dmp (1), Sb/tBu (2), and Bi/tBu (3), where Dmp=2,6-Me2C6H3) with various electron-deficient alkynes RC equivalent to CR &apos; (R/R &apos;=CO2Me (DMAD), R/R &apos;=H/CO2Me, or R/R &apos;=NC5F4) affords different types of heterocyclic compounds. In these reactions, 1-3 act as hidden dienes and participate in hetero-Diels-Alder (DA) reactions, a feature that has been only rarely reported for heavier pnictogen compounds. In this way, reactions of 1 furnished the set of 1-arsanaphthalenes 4-6. The most likely mechanism involves two steps, that is, an arsa-DA reaction giving a 1-arsa-1,4-dihydro-iminonaphthalene, followed by CH -&gt; NH proton migration. In contrast, this reaction sequence terminates at the first step in the case of the antimony analogue 2, thus giving the 1-stiba-1,4-dihydro-iminonaphthalenes 7 and 8. Reactions of the bismuth congener 3 gave one of two products depending on the alkyne used. Reaction of 3 with DMAD gave 1-bisma-1,4-dihydro-iminonaphthalene 9, whilst its reaction with two equivalents of HC equivalent to C(CO2Me) gave bismacyclohexadiene (10). All compounds have been characterized by NMR, IR, and Raman spectroscopies and X-ray diffraction analysis. The experimental data were complemented by a computational study, including a description of the reaction profiles of the hetero-DA reactions and an assessment of the aromaticities of the heterocyclic naphthalene derivatives.

  • 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

    2020

  • 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

    26

  • Issue of the periodical within the volume

    11

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    12

  • Pages from-to

    "1144 –1154"

  • UT code for WoS article

    000508068000001

  • EID of the result in the Scopus database

    2-s2.0-85078506740