Stereoselectivity of 1,1'-bi-2-naphtol synthesis using FeCl3

Križić, Ivana (2016) Stereoselectivity of 1,1'-bi-2-naphtol synthesis using FeCl3. Diploma thesis, Faculty of Science > Department of Chemistry.

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Abstract

Enantiomerically pure 1,1´–bi–2–naphthol and its derivatives have a wide usage as chiral catalysts in stereoselective organic synthesis. In this thesis aerobic oxidative fenolic coupling of 2–naphthol 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 1,1´–bi–2–naphthol using N–benzylcinchonidinium 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, N–benzylcinchoninium chloride, (S)–(–)–1–phenylethylamine, N–benzyl–(S)–3-hydroxyquinuclidium bromide, (S)–1–phenylethanol, methyl–β–D–glucopyranozide, β–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)- 1,1´–bi–2–naphthol, the reaction proceeded stereospecifically toward the (R)-enantiomer.

Item Type: Thesis (Diploma thesis)
Keywords: naphtol, chiral HPLC analysis, stereoselective synthesis
Supervisor: Primožič, Ines
Date: 2016
Number of Pages: 62
Subjects: NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Branka Maravic
Date Deposited: 21 Oct 2016 08:58
Last Modified: 21 Oct 2016 10:05
URI: http://digre.pmf.unizg.hr/id/eprint/5195

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