Acylation of Ferrocene with Adamantoyl Chloride and Cinnamoyl Chloride

Abstract

Liquid phase acylation of ferrocene with adamantoyl and cinnamoyl chloride was studied over different structural types of zeolites. The effect of the zeolite structure and acidity, and the influence of the reaction conditions on the ferrocene conversion and selectivity was investigated. The highest ferrocene conversions were achieved over zeolite Beta with Si/Al ratio 12.5 (cinnamoyl chloride 63.5%, adamantoyl chloride 45.9%). It was observed that with decreasing concentration of active sites in zeolite Beta the ferrocene conversion decreases. In addition, it was found that there is an optimum molar ratio of ferrocene to acylating agent, the ferrocene conversion increased with increasing temperature and amount of catalyst. The most important finding is that acylation of ferrocene with adamantoyl and cinnamoyl chloride leads exclusively to monoacylated products, most probably due to a deactivation of the cyclopentadiene rings after the attachment of the first acyl group.

An undergraduate research experience: Synthesis, modification, and comparison of hydrophobicity of zeolites A and X

“…The sharp band located at 978 cm -1 is due to the vibrations of Al-O and Si-O bonds, a characteristic that all zeolites share as an intrinsic property of their framework. Other bands located at 1650 cm -1 and 1450 cm -1 are due to the absorbed water and carbon monoxide, respectively, as by-products of a reaction between the zeolite, water, and air during the washing stage of the synthesis procedure [8,[18][19][20]. Lastly the broad band from 3000-3700 cm -1 is due to the O-H stretching within the zeolites.…”