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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/60461373:22810/19:43918555

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/LO1613" target="_blank" >LO1613: Výzkum nových materiálů pro chemický průmysl</a><br>

Návaznosti

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

Rok uplatnění

2019

Kód důvěrnosti údajů

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

Název periodika

Reaction Kinetics Mechanisms and Catalysis

ISSN

1878-5190

e-ISSN

—

Svazek periodika

126

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

10

Strana od-do

869-878

Kód UT WoS článku

000463627000020

EID výsledku v databázi Scopus

2-s2.0-85057160340