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master's thesis
Utjecaj veličine supstituenta na stereoselektivnost priprave derivata 3-metilenizoindolinona
Zagreb: University of Zagreb, Faculty of Science, 2022. urn:nbn:hr:217:730082
Duplić, Filip
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Duplić, F. (2022). Utjecaj veličine supstituenta na stereoselektivnost priprave derivata 3-metilenizoindolinona (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:730082

Duplić, Filip. "Utjecaj veličine supstituenta na stereoselektivnost priprave derivata 3-metilenizoindolinona." Master's thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:730082

Duplić, Filip. "Utjecaj veličine supstituenta na stereoselektivnost priprave derivata 3-metilenizoindolinona." Master's thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:730082

Duplić, F. (2022). 'Utjecaj veličine supstituenta na stereoselektivnost priprave derivata 3-metilenizoindolinona', Master's thesis, University of Zagreb, Faculty of Science, accessed 30 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:730082

Duplić F. Utjecaj veličine supstituenta na stereoselektivnost priprave derivata 3-metilenizoindolinona [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2022 [cited 2024 December 30] Available at: https://urn.nsk.hr/urn:nbn:hr:217:730082

F. Duplić, "Utjecaj veličine supstituenta na stereoselektivnost priprave derivata 3-metilenizoindolinona", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2022. Available at: https://urn.nsk.hr/urn:nbn:hr:217:730082

Metadata
TitleUtjecaj veličine supstituenta na stereoselektivnost priprave derivata 3-metilenizoindolinona
Title (english)Influence of substituent size on stereoselectivity of 3-methyleneisoindolinone derivative preparation
AuthorFilip Duplić
MentorMatija Gredičak (mentor)
Committee memberVesna Petrović Peroković (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 country2022-05-03, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U sklopu ovog diplomskog rada opisana je stereoselektivna priprava raznih 3- metilenizoindolinona katalitičkim dehidratiranjem odgovarajućih 3-alkilizoindolinonskih alkohola u prisutnosti Brønstedove kiseline. Istražen je utjecaj veličine supstituenta na atomu dušika na stereoselektivnost reakcije. Ako je na atomu dušika vezan atom vodika, nastaje Zizomer. S druge strane, kod supstituenta većeg volumena (metil, fenil, benzil i sl.), zbog nepovoljnih steričkih interakcija pretežito nastaje E-izomer. Polazni 3-alkilizoindolinonski alkoholi pripravljeni su adicijom Grignardovih reagensa na ftalimid i njegove derivate. Određeni su najpovoljniji reakcijski uvjeti dehidratiranja dobivenih alkohola, te je pomoću specifičnih reakcija dobiven uvid u mehanizam ove transformacije. Struktura svih pripravljenih spojeva potvrđena je analitičkim tehnikama i postupcima (NMR, MS, HPLC).
Abstract (english)
In this diploma thesis, the stereoselective preparation of various 3-methyleneisoindolinones by catalytic dehydration of the corresponding 3-alkylisoindolinone alcohols in the presence of Brønsted acid is described. The influence of the size of the substituent on the nitrogen atom on the stereoselectivity of the reaction was investigated. If a hydrogen atom is attached to a nitrogen atom, the Z-isomer is formed. In the case of a substituent of higher volume (methyl, phenyl, benzyl, etc.), due to unfavorable steric interactions, the E-isomer is predominantly formed. The starting 3-alkylisoindolinone alcohols were prepared by adding Grignard reagents to phthalimide and its derivatives. The most favorable reaction conditions for dehydration of the obtained alcohols were determined, and with the help of specific reactions, an insight into the mechanism of this transformation was obtained. The structure of all prepared compounds was confirmed by analytical techniques and procedures (NMR, MS, HPLC).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:730082
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
Terms of useLicence In copyright icon
Created on2022-05-11 11:39:05