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Pregled bibliografske jedinice broj: 389997

Zbornik radova

Autori: Matković, Marija; Basarić, Nikola; Mlinarić-Majerski, Kata; Singh, Ajeet; Ganguly, Bishwajit
Naslov: Hydrolysis and retro-aldol clevage of 2-(1-adamantyl)-3-hydroxybutanoate: competing reactions
Izvornik: XXI. hrvatski skup kemičara i kamijskih inženjeraTrogir, Hrvatska :
Skup: XXI. hrvatski skup kemičara i kamijskih inženjera
Mjesto i datum: Trogir, Hrvatska, 19-22.04.2009.
Ključne riječi: hydrolysis; retro-aldol reaction; threo- ethyl esters; erythro- ethyl esters
Sažetak:
In the scope of our research on the synthesis of peptides and peptidomimetics with embedded cage molecules [1], we have prepared adamantane analogue of ethyl 3-hydroxybutanoate [2]: threo-(1a) and erythro-(1b)-isomers of ethyl 2-(1-adamantyl)-3-hydroxybutanoate. In order to obtain the corresponding acid derivatives (2a) or (2b) [3], ethyl esters threo-1a and erythro-1b were submitted to the base hydrolysis. Surprisingly, the main product was 1-adamantylacetic acid (3), indicating that retro-aldol reaction [4] is in competition with hydrolysis. On the other hand, the parent compound without adamantyl substituent, ethyl 3-hydroxybutanoate (4) was efficiently hydrolyzed without retro-aldol reaction. To get more insight in significant difference observed in the base induced reactions of adamantyl derivatives 1a, 1b and parent ester 4, these reactions were studied by computational methods. Herein, the comparison of theoretical and experimental results will be presented.
Vrsta sudjelovanja: Poster
Vrsta prezentacije u zborniku: Sažetak
Vrsta recenzije: Domaća recenzija
Projekt / tema: 098-0982933-2911
Izvorni jezik: ENG
Kategorija: Znanstveni
Znanstvena područja:
Kemija
Upisao u CROSBI: eluksa@irb.hr (eluksa@irb.hr), 24. Tra. 2009. u 11:20 sati



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