Crown Ether Base: Highly Active, Regioselective and Reusable Catalytic Systems for Double Bond Migration in Allylic Compounds
PBN-AR
Instytucja
Instytut Chemii Organicznej Polskiej Akademii Nauk
Źródłowe zdarzenia ewaluacyjne
Informacje podstawowe
Główny język publikacji
en
Czasopismo
ChemistrySelect
ISSN
2365-6549
EISSN
Wydawca
ChemPubSoc Europe - Wiley VCH
DOI
Rok publikacji
2017
Numer zeszytu
23
Strony od-do
6717-6727
Numer tomu
2
Identyfikator DOI
Liczba arkuszy
Słowa kluczowe
en
allyl compounds
isomerization
one-pot isoxazolines synthesis
regioselective double bond migration
ultrasonication
Streszczenia
Język
en
Treść
The highly active, reusable and regioselective crown ethers bases catalytic systems, especially 15-Crown-5/NaOH, 18-Crown-6/KOH, dibenzo-18-Crown/6-t-BuOK, and 18-Crown-6/t-BuOK, for double bond migration in various allyl and diallyl compounds have been presented. Allyl and/or diallyl: arenes and heteroarenes, ethers, acetal, sulfides, selenide, sulfoxides, imines, phosphine, and phosphine oxide were smoothly converted into their corresponding 1-propenyl derivatives under very mild conditions. Some of the C,O- and O,S-diallyl compounds were fully regioselectively isomerized to allyl-(1-propenyl) derivatives. An unprecedented and significant effect of increasing the reaction rate and shortening the quantitative reaction conversion time without decreasing the selectivity under ultrasound-assisted conditions was observed. Various solvents, including low-boiling point ones containing only C, H and/or O atoms, such as DMFL, DME, THF, Et2O, toluene, and 1,4-dioxane, can be used instead of the most frequently used DMSO. Remarkably highly effective recycling of 18-Crown-6/t-BuOK and dibenzo-18-Crown-6-t-BuOK catalytic systems for isomerization of low-boiling or high-boiling point allyl compounds respectively and crown ethers from all examined catalytic systems was developed. The opportunity to effectively combine the double bond migration with in situ generation of nitrile oxide and finally 1,3-DC-cycloaddition into one pot variant synthesis of isoxazolines from Qallyl has also been announced.
Cechy publikacji
Original article
Original article presents the results of original research or experiment.
Oryginalny artykuł naukowy
Oryginalny artykuł naukowy przedstawia rezultaty oryginalnych badań naukowych lub eksperymentu.
Inne
System-identifier
PBN-R:857813
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