magistrsko delo
Abstract
V okviru magistrske naloge sem sintetiziral osem različno substituiranih biciklo[2.2.2]oktenskih sistemov z dvojno termično Diels–Alderjevo cikloadicijo maleinanhidrida na različno substituirane 2H-piran-2-one. V prvi stopnji s cikloadicijo maleinanhidrida v vlogi dienofila nastanejo oksabiciklo[2.2.2]oktenski intermediati, ki pod reakcijskimi pogoji spontano eliminirajo molekulo ogljikovega dioksida in tako tvorijo naslednji cikloheksadienski intermediat, ki služi kot nov dien za napad nove molekule dienofila (maleinanhidrida). Z molekulskim modeliranjem sem raziskal ali je v prvi stopnji cikloadicij različnih dienofilov (maleinanhidrida in substituiranih vinil etrov) reakcijski napad preferenčno ekso ali endo. Rezultate, dobljene z računsko metodo PM6, sem primerjal z eksperimentalnimi podatki, vključno z že objavljenimi v literaturi.
Keywords
organska sinteza;cikloadicija;Diels-Alderjeva reakcija;biciklo[2.2.2]oktenski sistemi;maleinanhidrid;2H-piran-2-oni;molekulsko modeliranje;magistrska dela;
Data
Language: |
Slovenian |
Year of publishing: |
2021 |
Typology: |
2.09 - Master's Thesis |
Organization: |
UL FKKT - Faculty of Chemistry and Chemical Technology |
Publisher: |
[A. Šinkovec] |
UDC: |
547.6(043.2) |
COBISS: |
76775171
|
Views: |
305 |
Downloads: |
40 |
Average score: |
0 (0 votes) |
Metadata: |
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Other data
Secondary language: |
English |
Secondary title: |
Synthesis of various substituted bicyclo[2.2.2]octene systems with the use of maleic anhydride and its derivatives |
Secondary abstract: |
In this master's degree I have synthesized eight variously substituted bicyclo[2.2.2]octene systems by using Diels–Alder cycloaddition of maleic anhydride on differently substituted 2H-pyran-2-ones. In the first stage of the cycloaddition of maleic anhydride as the dienophile oxabicyclo[2.2.2]octene intermediates are formed, which under the reaction conditions spontaneously eliminate a molecule of carbon dioxide and thus form the next cyclohexadiene intermediate, which serves as the diene for the attack of the second molecule of dienophile (maleic anhydride). Using molecular modelling I explored the endo/exo attack preference of various dienophiles (maleic anhydride and substituted vinyl ethers) of the first stage of the cycloaddition reaction. I compared the results, obtained with the computational method PM6, with experimental data in the literature. |
Secondary keywords: |
Diels-Alder reaction;bicyclo[2.2.2]octene;maleic anhydride;2H-pyran-2-one;molecular modelling; |
Type (COBISS): |
Master's thesis/paper |
Study programme: |
1000375 |
Embargo end date (OpenAIRE): |
1970-01-01 |
Thesis comment: |
Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo |
Pages: |
42 str. |
ID: |
13299909 |