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master's thesis
Priprava višesupstituiranih indena i spiroindena
Zagreb: University of Zagreb, Faculty of Science, 2022. urn:nbn:hr:217:720640
Šterpin, David
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Šterpin, D. (2022). Priprava višesupstituiranih indena i spiroindena (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:720640

Šterpin, David. "Priprava višesupstituiranih indena i spiroindena." Master's thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:720640

Šterpin, David. "Priprava višesupstituiranih indena i spiroindena." Master's thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:720640

Šterpin, D. (2022). 'Priprava višesupstituiranih indena i spiroindena', Master's thesis, University of Zagreb, Faculty of Science, accessed 21 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:720640

Šterpin D. Priprava višesupstituiranih indena i spiroindena [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2022 [cited 2024 December 21] Available at: https://urn.nsk.hr/urn:nbn:hr:217:720640

D. Šterpin, "Priprava višesupstituiranih indena i spiroindena", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2022. Available at: https://urn.nsk.hr/urn:nbn:hr:217:720640

Metadata
TitlePriprava višesupstituiranih indena i spiroindena
Title (english)Synthesis of multisupstituted indenes and spiroindenes
AuthorDavid Šterpin
MentorNikola Topolovčan (mentor)
Committee memberĐani Škalamera (predsjednik povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
Committee memberBiserka Prugovečki (član povjerenstva)
Committee memberŽeljka Car (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2022-12-16, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U okviru ovog diplomskog rada opisana je regioselektivna i kemoselektivna sinteza višesupstituiranih indena i spiroindena u nekoliko sintetskih koraka počevši od komercijalno dostupnih karbonilnih spojeva: benzofenona, 9-fluorenona i ftalimida. Sintetski put uključuje adiciju acetilida na odgovarajući karbonilni spoj pri čemu su dobiveni propargilni alkoholi prevedeni u željene produkte u sekvencijskim reakcijama Meyer-Schusterove pregradnje, funkcionalizacije dobivenih enona u alilne alkohole te intramolekulske Friedel-Craftsove alkilacije (Nazarov tip ciklizacije) u odgovarajući inden s naglaskom na kemoselektivnost i regioselektivnost reakcije ciklizacije. Također je provedena kemoselektivna i regioselektivna dvokomponentna reakcija između propargilnih alkohola i aromatskih nukleofila u svrhu priprave spiroindena. Strukture pripravljenih spojeva potvrđene su analitičkim tehnikama i postupcima (NMR, MS).
Abstract (english)
In this diploma thesis, regioselective and chemoselective synthesis of highly substituted indenes and spiroindenes starting from commercially available carbonyl compounds (benzophenone, 9- fluorenone and phtalimide) is described. Synthesis involves nucleophilic addition of various acetylenes, Meyer-Schuster rearragement of the prepared propargylic alcohols followed by the transformation of the corresponding enones to allylic alcohols, and finally Friedel-Crafts reaction of the allylic alcohols to afford the corresponding indenes. Furthermore, a regioselective and chemoselective two-component reaction of propargylic alcohols and nucleophilic aromatic compounds affording spiroindenes is described. Structures of all prepared compounds were confirmed by analytical techniques and procedures (NMR, MS).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:720640
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: Research programme
Course: Research 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
Embargo expiration date: 2023-06-16
Terms of useLicence In copyright icon
Created on2023-01-13 09:30:06