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master's thesis
Priprava višesupstituiranih ciklopentadiena cirkonocenom potpomognutom ciklizacijom dienina
Zagreb: University of Zagreb, Faculty of Science, 2023. urn:nbn:hr:217:118344
Gobin, Marko
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Gobin, M. (2023). Priprava višesupstituiranih ciklopentadiena cirkonocenom potpomognutom ciklizacijom dienina (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:118344

Gobin, Marko. "Priprava višesupstituiranih ciklopentadiena cirkonocenom potpomognutom ciklizacijom dienina." Master's thesis, University of Zagreb, Faculty of Science, 2023. https://urn.nsk.hr/urn:nbn:hr:217:118344

Gobin, Marko. "Priprava višesupstituiranih ciklopentadiena cirkonocenom potpomognutom ciklizacijom dienina." Master's thesis, University of Zagreb, Faculty of Science, 2023. https://urn.nsk.hr/urn:nbn:hr:217:118344

Gobin, M. (2023). 'Priprava višesupstituiranih ciklopentadiena cirkonocenom potpomognutom ciklizacijom dienina', Master's thesis, University of Zagreb, Faculty of Science, accessed 21 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:118344

Gobin M. Priprava višesupstituiranih ciklopentadiena cirkonocenom potpomognutom ciklizacijom dienina [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2023 [cited 2024 December 21] Available at: https://urn.nsk.hr/urn:nbn:hr:217:118344

M. Gobin, "Priprava višesupstituiranih ciklopentadiena cirkonocenom potpomognutom ciklizacijom dienina", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2023. Available at: https://urn.nsk.hr/urn:nbn:hr:217:118344

Metadata
TitlePriprava višesupstituiranih ciklopentadiena cirkonocenom potpomognutom ciklizacijom dienina
Title (english)Synthesis of multisusbstituted cyclopentadienes by zirconocene-mediated cyclization of dienynes
AuthorMarko Gobin
MentorNikola Topolovčan (mentor)
Committee memberĐani Škalamera (predsjednik povjerenstva)
Committee memberAleksandra Maršavelski (član povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2023-11-22, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U okviru ovog diplomskog rada razvijena je metodologija priprave višesupstituiranih ciklopentadiena u nekoliko konvergentnih sintetskih koraka pri čemu postoji mogućnost selektivnog uvođenja i variranja veličine pojedinih supstituenata na ciklopentadienskom prstenu. Sintetski put započinje regioselektivnom bromalilacijom disupstituiranih alkina pri čemu nastaju odgovarajući bromdieni s reaktivnom ugljik-halogen vezom. To je ključno za provedbu Sonogashirine reakcije s terminalnim acetilenima kako bi se generirali nekonjugirani dienini. Ciklizacijom dienina pomoću niskovalentnog organocirkonija (Negishijev reagens) pripravljeni su ciklopentadieni s exo-cikličkom dvostrukom. U posljednjem koraku, kiselinom kataliziranom exo-to-endo izomerizacijom exo-cikličke dvostruke veze ciklopentadiena pripravljeni su tetrasupstituirani ciklopentadieni. Strukture pripravljenih spojeva potvrđene su analitičkim tehnikama i postupcima (NMR, MS).
Abstract (english)
The methodology for the preparation of multisubstituted cyclopentadienes in several convergent synthesis steps was developed within this master's thesis. This allows for the selective introduction and varation of the size of individual substituents on the cyclopentadienyl ring. The synthetic route starts with the regioselective bromallylation of disubstituted alkynes, yielding the corresponding bromodienes with a reactive carbon-halogen bond, which is crucial for carrying out the Sonogashira reaction with terminal acetylenes to generate non-conjugated dienynes. By cyclizing the dienyne using low-valent zirconium compounds (Negishi reagent), cyclopentadienes with an exo-cyclic double bond were prepared. In final step, through acid catalyzed exo-to-endo isomerisation of the exo-cyclic double bond of the cyclopentadiene, tetrasubstituted cyclopentadienes were prepared. The structures of the prepared compounds were confirmed using analytical techniques and procedures such as (NMR, MS).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:118344
ProjectNumber: IP-2018-01-4053
Title: Nove strategije za pripravu tetrasupstituiranih kiralnih centara: asimetrične katalitičke reakcije usmjerene protuanionom
Acronym: NSYNC-ACDC
Leader: Matija Gredičak
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
Study programmeTitle: Graduate university studies in chemistry; specializations in: Graduate university studies in chemistry
Course: Graduate university studies in chemistry
Study programme type: university
Study level: graduate
Academic / professional title: sveučilišni/a magistar/magistra kemije (sveučilišni/a magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2024-05-22
Terms of useLicence In copyright icon
Created on2023-11-27 11:53:05