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 ' (R/R '=CO2Me (DMAD), R/R '=H/CO2Me, or R/R '=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 -> 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
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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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
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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