magistrsko delo
Matic Rogan (Author), Marjan Jereb (Mentor), Franc Požgan (Thesis defence commission member), Martin Gazvoda (Thesis defence commission member)

Abstract

V sklopu magistrske naloge sem preko tristopenjske sinteze pripravil trideset vmesnih 1,3-eninov in osemnajst končnih fluoro hidroksiliranih in fluoro alkoksiliranih produktov, ki so bili v tekočem ali trdnem agregatnem stanju. Prva stopnja je bila sinteza različno substituiranih propargilnih alkoholov, te reakcije sem izvedel brez uporabe topil, ki sem jih v nadaljevanju z eliminacijo vode pretvoril v 1,3-enine. Ti vsebujejo dve konjugirani π-vezi, dvojno in trojno, zato nas je, poleg vpliva različnih funkcionalnih skupin, zanimal tudi njun vpliv na nadaljnje pretvorbe s Selectfluor™. Selectfluor™ je komercialno dostopen reagent za selektivno uvedbo fluorovega atoma, ki je hkrati tudi relativno močan oksidant. V primeru poteka reakcije v acetonitrilu v kombinaciji z vodo kot nukleofilom, so nastali adicijski fluoro hidroksi derivati, zato sem študiral tudi uporabo drugih nukleofilov, alkoholov, in sintetiziral nekatere fluoro alkoksidne produkte.

Keywords

propargilni alkoholi;reakcijski pogoji brez uporabe topil;1,3-enini;Selectfluor;elektrofilno fluoriranje;vez C-F;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [M. Rogan]
UDC: 547.1:66.094.412(043.2)
COBISS: 86666243 Link will open in a new window
Views: 163
Downloads: 33
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Other data

Secondary language: English
Secondary title: Synthesis and conversions of selected substituted alkynes
Secondary abstract: In my master's thesis, I have synthesized thirty intermediate 1,3-enynes and eighteen final fluoro-hydroxy and fluoro-alkoxy products in liquid or solid state through a three-stage synthesis. The first stage was the synthesis of variously substituted propargyl alcohols under solvent-free conditions, which I later converted to 1,3-enynes by elimination. These contain two conjugated π-bonds, a double and a triple bond, so in addition to the influence of various functional groups, I was interested in their impact on later conversions using Selectfluor™. Selectfluor™ is a commercially available reagent for selective introduction of fluorine atom and relatively strong oxidant. In the case of the reaction taking place in acetonitrile in combination with water as the source of the nucleophile, the products were fluoro-hydroxy adducts, so I further examined the use of other nucleophiles, alcohols, and synthesized some alkoxy products.
Secondary keywords: propargylic alcohols;solvent-free conditions;1,3-enynes;electrophilic fluorination;
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, smer Kemija
Pages: 63 str.
ID: 13587548