Naslov
Ferrocene Compounds. XXXVII. Reactions of 1, 1'-Ferrocenylenebis(carbinyl acetates) and Derived Quaternary Iodides with Methyl salicylate

Autori
Kovač, Veronika ; Rapić, Vladimir ; Kovaček, Damir

Izvornik
Croatica Chemica Acta (0011-1643) 76 (2003); 347-355

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
alpha; alpha'-(1; 1'-ferrocenylene)biscarbinols; alpha; alpha'-(1; 1'-ferrocenylene)bis-(carbinyl acetates) and derived quaternary iodides; O- and C-ferrocylation; methyl salicylate; ab initio; DFT

Sažetak
Acetates 1 were prepared from corresponding biscarbinols according to the described procedures. Iodides 3 were obtained by quaternization of the corresponding amines 2 with methyl iodide in acetone. A solution of reagents 1a (3a) in an excess of methyl salicylate containing 6 moles of sodium was refluxed for 2 hours, giving 4a [8 (14)%] and 5a [10 (15)%]. Under the similar conditions 1b (3b) gave 4b [10 (3)%] and 5b [4 (9)%], followed by elimination products 7 and 8. Similarly, acetate 1c was transformed into 4c (8%), 5c (15%) and 6c (6%). Structure of heteroannularly substituted nonsymetric ferrocene derivatives 4-8 was undoubtedly confirmed on the basis of elemental and spectroscopic analysis, and the reaction mechanisms of their formation were proposed. Ab initio MO calculations of the ground states were performed to elucidate the character of the hydrogen bonding and stability of disubstituted ferrocene compounds 4-6.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA