Naslov
Mechanism of the biomimetic cyclopentyl ring expansion

Autori
Vrček, Valerije ; Kronja, Olga

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Skup
8th European symposium on organic reactivity

Mjesto i datum
Cavtat, Hrvatska, 01.09.2001. - 06.09.2001

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
carbocation; rearrangement; computational chemistry

Sažetak
In order to investigate the mechanism of the five-membered ring enlargement in carbocation intermediates in steroid biosynthesis, the rearrangement processes in a model carbocation, the 2-cyclopentyl-2-propyl cation 5, were followed by means of 1H and 13C NMR spectroscopy. Carbocations 5A and 5B were prepared in SbF5– SO2ClF–SO2F2 from the corresponding alcohol precursors. At about ÿ100°C a ring enlargement process takes place to give the 1, 2-dimethylcyclohexyl cation 7. Quantum chemical calculations of model carbocation structures 5A, 5B, 6 and 7 were carried out at the HF/6–31G(d) and B3LYP/6–31G(d) levels of theory.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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