Original scientific paper

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

Veronika Kovač ; Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia
Vladimir Rapić ; Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia
Damir Kovaček ; Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia

Abstract

Acetates 1 were prepared from appropriate biscarbinols according to described procedures. Iodides 3 were obtained by quaternization of appropriate 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 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 %). The structure of heteroannularly substituted unsymmetrical ferrocene derivatives 4–8 was undoubtedly confirmed on the basis of elemental and spectroscopic analyses, and the reaction mechanisms of their formation were proposed. Ab initio MO calculations of the ground states were performed to elucidate the character of hydrogen bonding and the stability of disubstituted ferrocene compounds 4–6.

Keywords

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

Hrčak ID:

103198

URI

https://hrcak.srce.hr/103198

Publication date:

28.11.2003.

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