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master's thesis
Stereoselektivnost sinteza 1,1'-bi-2-naftola u reakcijama s FeCl3
Zagreb: University of Zagreb, Faculty of Science, 2016. urn:nbn:hr:217:983365
Križić, Ivana
University of Zagreb
Faculty of Science
Department of Chemistry

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Križić, I. (2016). Stereoselektivnost sinteza 1,1'-bi-2-naftola u reakcijama s FeCl3 (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:983365

Križić, Ivana. "Stereoselektivnost sinteza 1,1'-bi-2-naftola u reakcijama s FeCl3." Master's thesis, University of Zagreb, Faculty of Science, 2016. https://urn.nsk.hr/urn:nbn:hr:217:983365

Križić, Ivana. "Stereoselektivnost sinteza 1,1'-bi-2-naftola u reakcijama s FeCl3." Master's thesis, University of Zagreb, Faculty of Science, 2016. https://urn.nsk.hr/urn:nbn:hr:217:983365

Križić, I. (2016). 'Stereoselektivnost sinteza 1,1'-bi-2-naftola u reakcijama s FeCl3', Master's thesis, University of Zagreb, Faculty of Science, accessed 16 April 2024, https://urn.nsk.hr/urn:nbn:hr:217:983365

Križić I. Stereoselektivnost sinteza 1,1'-bi-2-naftola u reakcijama s FeCl3 [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2016 [cited 2024 April 16] Available at: https://urn.nsk.hr/urn:nbn:hr:217:983365

I. Križić, "Stereoselektivnost sinteza 1,1'-bi-2-naftola u reakcijama s FeCl3", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2016. Available at: https://urn.nsk.hr/urn:nbn:hr:217:983365

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Metadata
TitleStereoselektivnost sinteza 1,1'-bi-2-naftola u reakcijama s FeCl3
Title (english)Stereoselectivity of 1,1'-bi-2-naphthol syntheses using FeCl3
AuthorIvana Križić
MentorInes Primožič (mentor)
Committee memberInes Primožič (predsjednik povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
Committee memberBiserka Prugovečki (član povjerenstva)
Committee memberIvana Biljan (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2016-09-27, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
Enantiomerno čisti 1,1bi2naftol te njegovi derivati imaju široku primjenu kao kiralni katalizatori u stereoselektivnim organskim sintezama. U ovom radu istražena je priprava 1,1bi2naftola u reakciji oksidativnog fenolnog povezivanja 2-naftola uz Fe(III) klorid uz prisustvo zraka, u organskim otapalima i mehanokemijski, uz katalitičku količinu otapala. Optimirani su uvjeti reakcije u metanolu, acetonu i acetonitrilu. Reakcija je bitno ubrzana dodatkom di-tert-butilperoksida. Mehanokemijska sinteza (LAG) nije se pokazala kao dobra metoda za izvođenje reakcije. Sintetiziranom racemičnom 1,1bi2naftolu razdvojeni su enantiomeri kemijskom metodom s Nbenzilcinhonidinijevim kloridom. Da bi istražili moguće postizanje stereoselektivnosti reakcije (acetonitril/di-tert-butilperoksid) u reakcijsku smjesu dodan je niz kiralnih spojeva (cinchonidin, cinhonin, Nbenzilcinhoninijev klorid, (S)()1feniletilamin, Nbenzil(S)3-hidroksikinuklidinijev bromid, (S)1feniletanol, metilDglukopiranozid, cikodekstrin) te HPLC metodom na kiralnoj koloni praćena inducirana stereoselektivnost reakcije. Najbolja stereoselektivnost pokazala se u reakciji s (S)-1-feniletilaminom (e.v. 14,4 %). Reakcija priprave 1,1bi2naftola izvedena je i uz dodatak jednog od produkata reakcije, (S)enantiomera. Dobiven je stereospecifično kao produkt (R)enantiomer.
Abstract (english)
Enantiomerically pure 1,1bi2naphthol and its derivatives have a wide usage as chiral catalysts in stereoselective organic synthesis. In this thesis aerobic oxidative fenolic coupling of 2naphthol with Fe(III) chloride in organic solvents was investigated. Reaction was performed in methanol, acetonitrile and acetone successfully. Addition of di-tert-butylperoxide significantly speeded up the reaction. Mechanochemical synthesis (LAG) was investigated as well, but under the used experimental conditions no product was observed. Chemical resolution of racemic 1,1bi2naphthol using Nbenzylcinchonidinium chloride was performed to gain pure enantiomers. To evaluate possible stereoselectivity of the reaction (acetonitrile/di-tert-butylperoxide), a series of chiral compounds were added as well: cinchonidine, cinchonine, Nbenzylcinchoninium chloride, (S)()1phenylethylamine, Nbenzyl(S)3-hydroxyquinuclidium bromide, (S)1phenylethanol, methylDglucopyranozide, cyclodextrin. Chiral HPLC method was used to detect induced stereoselectivity of reactions. In the reaction with (S)-1-feniletilamine, the best stereoselectivity was observed (ee 14.4 %). When the stereoselective reaction was conducted in the presence of the product, (S)- 1,1bi2naphthol, the reaction proceeded stereospecifically toward the (R)-enantiomer.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:983365
Study programmeTitle: Graduate Studies in Chemistry; specializations in: Research (scientific-professional) programme
Course: Research (scientific-professional) programme
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
RepositoryRepository of the Faculty of Science
Created on2017-01-26 09:31:08

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