Epoksidacija in nadaljnje pretvorbe Weinrebovega amida (+)-izokamfolenske kisline

Stražiščar, Katja (author), Grošelj, Uroš (mentor)

Iz (+)-izokamfolenske kisline sem pripravila Weinrebov amid, ki sem ga pretvorila v ustrezen epoksid s pomočjo 3-kloroperoksibenzojske kisline. V nadaljnjem koraku sem poskusila odpreti epoksid na manj substituirani strani z uporabo kalijevega hidroksida. Reakcija ni potekla, saj se je Weinrebov amid hidroliziral. Da bi odpravila težavo s hidrolizo, sem amidno skupino zamenjala z eterno, ki je stabilnejša. Nato sem postopek epoksidacije in odprtja epoksida ponovno izvedla, tokrat pod bazičnimi pogoji in nato pod kislimi pogoji.

• Language: Slovenian
• Keywords: Weinrebov amid, (+)-izokamfolenska kislina, epoksidacija, odprtje epoksida, molekulske premestitve
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2023
• PID: 20.500.12556/RUL-149557
• COBISS.SI-ID: 164580355
• Publication date in RUL: 07.09.2023

Secondary language

• Language: English
• Title: Epoxidation and further transformations of (+)-isocampholenic acid derived Weinreb amide

Abstract

I prepared the Weinreb amide from (+)-isocampholenic acid, which I then converted into the corresponding epoxide using 3-chloroperoxybenzoic acid. In the next step, I attempted to open the epoxide on the less substituted side using potassium hydroxide. However, the reaction did not proceed only the Weinreb amide hydrolyzed. To overcome this problem, I replaced the amide side group with an ether group, which is more stable, and repeated the epoxidation and epoxide opening reactions, first under basic and then under acidic conditions.

• Keywords: Weinreb amide, (+)-isocampholenic acid, epoxidation, epoxide ring opening, molecular rearrangement