A convenient method for synthesis of novel alkylferrocene derivatives with various functional groups: synthesis, charact
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ORIGINAL PAPER
A convenient method for synthesis of novel alkylferrocene derivatives with various functional groups: synthesis, characterization and electrochemical investigation Reza Teimuri‑Mofrad1 · Alireza Aghaiepour1 · Keshvar Rahimpour1 Received: 28 January 2020 / Accepted: 11 April 2020 © Iranian Chemical Society 2020
Abstract In this research, new ferrocenylmethylesters were synthesized according to esterification reaction. To reach this purpose, direct and indirect esterification methods were used. Indirect method included Cannizzaro reaction of new alkylferrocenecarboxaldehydes result in production of alkylferrocenecarboxylic acids and alkyl(hydroxymethyl)ferrocene derivatives. Finally, a variety of known procedures were used for converting the new alkylferrocenecarboxylic acids to the corresponding esters. The oxidative esterification reaction was accomplished using K2CO3/I2 as oxidant in the direct method. The advantages of this method are one-pot and single-step reaction and remarkably high total yield of this procedure. The chemical structures were confirmed with FT-IR, 1H NMR, 13C NMR and MASS spectroscopy as well as CHN analysis. Electrochemical behavior of synthesized compounds was studied by cyclic voltammetry, and the relationship between the peak currents and the square root of the scan rate showed that the redox process is diffusion-limited.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13738-020-01938-7) contains supplementary material, which is available to authorized users. * Reza Teimuri‑Mofrad [email protected] 1
Department of Organic and Biochemistry Faculty of Chemistry, University of Tabriz, Tabriz 51664, Iran
13
Vol.:(0123456789)
Journal of the Iranian Chemical Society
Graphic abstract
Keywords Alkylferrocene derivatives · Oxidative esterification · Disubstituted isomers · Cannizzaro reaction · Methyl esters
Introduction Aldehydes especially aromatic aldehydes have attracted much attention as essential intermediates in chemistry because of their high applicable potential in industry and science; pharmaceutical chemistry [1] and fine chemicals for fragrances or flavorings are modest examples of their applications [2]. The outstanding feature of aldehydes is the ability of them in converting to other functional groups such as alcohols, carboxylic acid, alkenes, esters, etc. Classically, esters were generated from the reaction of carboxylic acids with alcohols [3]. Nowadays, we know that oxidation of aldehydes with an appropriate oxidant such as oxone (KHSO5) or peroxy monosulfuric acid ( H2SO5) in the presence of alcohol as solvent generated corresponding esters in high yields [4]. The oxidative esterification reaction is a well-known one-pot reaction which has been done with a variety of oxidative reagents and was performed using different methods in kinds of literature [5, 6]. Simplicity, one-pot reaction, and economic efficiency caused the oxidative esterification reaction can be attracted considerable atte
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