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Methyltrioxorhenium as a Lewis Acid in the Prins Cyclization of Benzaldehyde and Isoprenol

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F19%3A43918555" target="_blank" >RIV/60461373:22310/19:43918555 - isvavai.cz</a>

  • Alternative codes found

    RIV/60461373:22810/19:43918555

  • Result on the web

    <a href="https://link.springer.com/content/pdf/10.1007%2Fs11144-018-1503-0.pdf" target="_blank" >https://link.springer.com/content/pdf/10.1007%2Fs11144-018-1503-0.pdf</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1007/s11144-018-1503-0" target="_blank" >10.1007/s11144-018-1503-0</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Methyltrioxorhenium as a Lewis Acid in the Prins Cyclization of Benzaldehyde and Isoprenol

  • Original language description

    Methyltrioxorhenium (MTO) as a Lewis acid was used in the acid catalyzed reaction of benzaldehyde and isoprenol leading to the formation of 4-methyl-2-phenyl-tetrahydro-2H-pyran-4-ol. The influence of reaction conditions on the reaction course was investigated. Under optimal reaction conditions (70 °C, a molar ratio of reactants 1:1, 1 wt% of MTO, no solvent, 100 mol% of water) the selectivity to desired product was 76%. The addition of water to the reaction mixture evoked the decrease of the reaction rate and slight increase of selectivity (without water addition the selectivity was approximately 70%). The typical composition of isomers of the desired product was cis:trans = 30:70. The mechanism of Prins cyclization using methyltrioxorhenium as the catalyst was offered. This mechanism explains the low concentration of intermediate hemiacetal in the reaction mixture using MTO as the catalyst. MTO was also heterogenized on silica, alumosilicate and alumina support. Characterization confirmed the successful attachment and homogeneous distribution of MTO on the supports, but kinetic measurement showed high leaching of MTO from pure silica and aluminosilicate support. MTO/alumina was reused with a low decrease of conversion. © 2018, Akadémiai Kiadó, Budapest, Hungary.

  • 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

    10401 - Organic chemistry

Result continuities

  • Project

    <a href="/en/project/LO1613" target="_blank" >LO1613: Future materials</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Others

  • Publication year

    2019

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Reaction Kinetics Mechanisms and Catalysis

  • ISSN

    1878-5190

  • e-ISSN

  • Volume of the periodical

    126

  • Issue of the periodical within the volume

    2

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    10

  • Pages from-to

    869-878

  • UT code for WoS article

    000463627000020

  • EID of the result in the Scopus database

    2-s2.0-85057160340