Sinteza (R)-4-(2-bromoetil)-1,5,5-trimetilciklopent-1-ena

Jamnik, Lana (author), Grošelj, Uroš (mentor)

V diplomski nalogi sem opisala eno od možnih sinteznih poti do (R)-2-(2-bromoetil)-1,1-dimetil-5-metilenciklopentana iz komercialno lahko dostopne kafre. Opisala sem vse sintezne korake s poudarkom na Appelovi reakciji. Večji del te sinteze sem izvedla tudi v laboratoriju. Pripravila sem (R)-4-(2-bromoetil)-1,5,5-trimetilciklopent-1-en iz (1S)-(+)-10-kafrasulfonske kisline. Sintezo sem izvedla v štirih korakih preko (+)-izokamfolenske kisline, ki nastane z Grobovo fragmentacijo. Ključni korak sinteze je bila tvorba bromida iz alkohola pod blagimi reakcijskimi pogoji, ki jih zagotavlja Appelova reakcija.

• Language: Slovenian
• Keywords: kafra, kafrasulfonska kislina, Grobova fragmentacija, Appelova reakcija.
• 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-147072
• COBISS.SI-ID: 159909635
• Publication date in RUL: 22.06.2023

Secondary language

• Language: English
• Title: Synthesis of (R)-4-(2-bromoethyl)-1,5,5-trimethylcyclopent-1-ene

Abstract

In my thesis, I described one of the possible synthesis routes of (R)-2-(2-bromoethyl)-1,1-dimethyl-5-methylenecyclopentane from commercially readily available camphor. I described all the synthesis steps, with an emphasis on the Appel reaction. I also carried out the major part of this synthesis in the laboratory. I prepared (R)-4-(2-bromoethyl)-1,5,5-trimethylcyclopent-1-ene from (1S)-(+)-10-camphorsulfonic acid. I carried out the synthesis in four steps via (+)-isocampholenic acid, which is formed by Grob fragmentation. The key step of the synthesis was the formation of the bromide from the alcohol under mild reaction conditions provided by the Appel reaction.

• Keywords: camphor, camphorsulfonic acid, Grob fragmentation, Appel reaction.