Utjecaj veličine supstituenta na stereoselektivnost priprave derivata 3-metilenizoindolinona

master's thesis

• Title (english): Influence of substituent size on stereoselectivity of 3-methyleneisoindolinone derivative preparation
• Author: Filip Duplić
• Mentor: Matija Gredičak (mentor)
• Committee member: Vesna Petrović Peroković (predsjednik povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Biserka Prugovečki (član povjerenstva)
• Committee member: Željka Car (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2022-05-03, 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: Brønstedova kiselina; katalitičko dehidratiranje; 3-metilenizoindolinoni; stereoselektivnost; sterički utjecaj supstituenta na dušiku
• Keywords (english): Brønsted acid; catalytic dehydration; 3-methyleneisoindolinones; stereoselectivity; steric influence of substituent on nitrogen
• Language: croatian
• URN:NBN: urn:nbn:hr:217:730082
• Project: Number: 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 programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2022-05-11 11:39:05