Naslov
EXPERIMENTAL AND COMPUTATIONAL STUDY OF THE REACTION BETWEEN FERROCENYL LITHIUM AND N-PHENYL PHTHALIMIDE

Autori
Vrček, Valerije ; Grumbt, Martin ; Schaarschmidt, Dieter ; Šakić, Davor ; Alexander Hildebrandt

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

Izvornik
17th European Symposium on Organic Reactivity 2019 - Book of Abstracts / Vančik, Hrvoj ; Namjesnik, Danijel - Zagreb : Hrvatsko kemijsko društvo, 2019, 97-97

ISBN
978-953-55232-9-1

Skup
17th European Symposium on Organic Reactivity (ESOR 2019)

Mjesto i datum
Dubrovnik, Hrvatska, 08.09.2019. - 13.09.2019

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
ferrocene, ftalidimide, DFT

Sažetak
In order to investigate the electronic and structural interactions between organometallic functionalities and heterocycles, [1, 2] a reaction between ferrocenyl lithium (FcLi) and N-phenyl phthalimide (1) was performed. During the course of this reaction an unusual reactivity was observed. The conversion of one equivalent of FcLi with 1, resulted in mono-ferrocenyl lactam 2, which rapidly undergoes ring-chain tautomerism 2  3. When two equivalents of FcLi were used, a bis-ferrocenyl lactone 4, involving a five-membered oxygen bridged heterocycle, was formed. In addition, a tricyclic product 5, in which one of the ferrocene moieties displays a planar chiral substitution pattern, was isolated. The compounds 2 – 5 were characterized spectroscopically and electrochemically. The molecular structures in solid state were defined by X-ray diffraction analysis. The involved reaction mechanisms were explored by use of modern density functional techniques.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija

POVEZANOST RADA