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Uporaba elektrokemijskih metod v organski sintezi za tvorbo pinakolne vezi iz substituiranih aldehidov ali ketonov
ID Ponikvar, Žiga (Author), ID Kranjc, Krištof (Mentor) More about this mentor... This link opens in a new window

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Abstract
V magistrskem delu so predstavljene elektrokemijske sinteze pinakola in njegovih derivatov. Osredotočil sem se na konstrukcijo in uporabo nedeljene elektrolizne celice; želel sem uporabiti lahko dosegljive materiale in cenovno dostopne napajalnike, ki pa za primerno delovanje vendarle potrebujejo nekaj modifikacij. V nadaljevanju sem s pomočjo sestavljene celice želel ugotoviti, kateri elektrodni materiali omogočajo tvorbo pinakolne vezi med uporabljenimi aldehidi ali ketoni in kako pripraviti elektrolit, ki obenem omogoča dovolj visoke tokove ter ne vpliva na potek same sinteze. Zanimal me je tudi vpliv uporabljenega potenciala, saj ima velik vpliv na selektivnost in morebitne stranske reakcije. Reakcijske zmesi in produkte sem ovrednotil s TLC in spektroskopskimi metodami (1H NMR, HRMS). Ugotovil sem, da ima nedeljena celica zgolj omejene možnosti uporabe, vendar lahko z uporabo navadnih železnih elektrod pod milimi pogoji iz aromatskih aldehidov vseeno sintetiziramo vicinalne diole.

Language:Slovenian
Keywords:pinakol, simetrična organska elektrokemijska sinteza, reduktivno spajanje, nedeljena elektrolizna celica, dvoelektrodni sistem
Work type:Master's thesis/paper
Typology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2020
PID:20.500.12556/RUL-119137 This link opens in a new window
COBISS.SI-ID:27903491 This link opens in a new window
Publication date in RUL:03.09.2020
Views:1053
Downloads:183
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Secondary language

Language:English
Title:Application of electrochemical methods in organic synsthesis for pinacol bond formation from substituted aldehydes or ketones
Abstract:
In this master’s thesis, I present some electrochemical methods that can be applied for the synthesis of pinacol and its derivatives. I focused on the construction and use of an undivided electrolysis cell by utilizing easily obtainable materials and cost-effective power supply units, albeit they require some modifications before the eventual use. The next goal was to use the assembled cell and investigate which electrode materials enable pinacol bond formation between the chosen aldehydes or ketones. Another question was how to prepare an electrolyte that enables sufficient currents without negatively impacting the synthesis. I was also interested in the applied voltage potentials, how they influence the selectivity, and possibly foster side reactions. Reaction mixtures and products were characterized by TLC and spectroscopic methods (1H NMR, HRMS). The conclusion is that an undivided cell has only limited application, however, when used in conjunction with ordinary iron electrodes, it may still be successfully used to synthesize vicinal diols from aromatic aldehydes under mild conditions.

Keywords:pinacol, symmetrical organic electrochemical synthesis, reductive coupling, undivided cell, two-electrode system

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