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

diplomsko delo

Katja Stražiščar (Author), Uroš Grošelj (Mentor)

Abstract

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.

Keywords

kafra;(+)-izokamfolenska kislina;Weinrebov amid;odprtje epoksida;molekulske premestitve;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2023
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[K. Stražiščar]
UDC:	547.599.6:66.094.39(043.2)
COBISS:	164580355
Views:	34
Downloads:	13
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Epoxidation and further transformations of (+)-isocampholenic acid derived Weinreb amide
Secondary 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.
Secondary keywords:	Weinreb amide;(+)-isocampholenic acid;epoxidation;epoxide ring opening;molecular rearrangement;Amidi;Epoksidiranje;Univerzitetna in visokošolska dela;
Type (COBISS):	Bachelor thesis/paper
Study programme:	1000373
Embargo end date (OpenAIRE):	1970-01-01
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages:	38 str.
ID:	19908997