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Organokatalizirana adicija tetronske kisline na nitroalkene na osnovi nasičenih maščobnih kislin
ID Fister, Martin (Author), ID Grošelj, Uroš (Mentor) More about this mentor... This link opens in a new window

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Abstract
V diplomski nalogi sem opisal eno od možnih sinteznih poti do 1-nitroheptadek-1-ena iz komercialno dostopne palmitinske kisline ter sledečo Michaelovo adicijo tetronske kisline na nitroalken. Opisane korake sinteze sem izvedel tudi v laboratoriju, kjer sem celotno sintezo nitroalkena ponovil dvakrat, da bi primerjal rezultate med ponovitvama. Sintezo sem izvedel v petih korakih preko heksadekanala ter 1-nitroheptadekan-2-ola, ki nastane s Henryjevo adicijo nitrometana na heksadekanal. Ključni korak sinteze je končna Michaelova adicija, ki jo lahko z uporabo akiralnega organokatalizatorja izvedemo pri blagih pogojih z visokim izkoristkom.

Language:Slovenian
Keywords:nitroalken, tetronska kislina, Michaelova adicija, Henryjeva reakcija, organokatalizator
Work type:Bachelor thesis/paper
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2024
PID:20.500.12556/RUL-161325 This link opens in a new window
Publication date in RUL:10.09.2024
Views:88
Downloads:15
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Secondary language

Language:English
Title:Organocatalyzed addition of tetronic acid to fatty acid-derived nitroalkenes
Abstract:
In my thesis, I described one of the possible synthesis routes of 1-nitroheptadec-1-ene from commercially available palmitic acid and the Michael addition of the tetronic acid to nitroalkene. I conducted the described synthesis in the laboratory, where I carried out the synthesis of the nitroalkene twice in order to compare the results of the two iterations. I carried out the synthesis in five steps via hexadecanal and 1-nitroheptadecan-2-ol, that was formed during the Henry addition of nitromethane to hexadecanal. The key step of the synthesis was the Michael addition, which was carried out under mild reaction conditions and with a high yield using achiral organocatalyst.

Keywords:nitroalkene, tetronic acid, Michael addition, Henry reaction, organocatalyst

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