Fructose-catalyzed synthesis of tetrahydrobenzo[b]pyran derivatives: Investigation of kinetics and mechanism

doi:10.1016/S1872-2067(14)60302-8

Abstract

Abstract:

Fructose was used as an efficient catalyst for three-component condensation reactions of aryl aldehydes, malononitrile, and dimedone in a mixture of EtOH and H₂O as green solvents. The advantages of this method are a short reaction time, high yields, low cost, easy accesses, and simple work-up. The mechanism of the synthesis of a derivative of 4H-tetrahydrobenzo[b]pyran was clarified using spectroscopic kinetic methods. The activation energy (E_a = 65.34 kJ/mol) and related kinetic parameters (ΔG^‡ = 69.14 kJ/mol, ΔS^‡ = 20.99 J/(mol·K), and ΔH^‡ = 62.89 kJ/mol) were calculated, based on the effects of temperature, concentration, and solvent. The first step in the proposed mechanism was identified as the rate-determining step (k₁), based on the steady-state approximation.

Key words: Fructose, Catalyst, Kinetics, Mechanism, Tetrahydrobenzo[b]pyran derivative

Sayyedeh Shadfar Pourpanah, Sayyed Mostafa Habibi-Khorassani, Mehdi Shahraki. Fructose-catalyzed synthesis of tetrahydrobenzo[b]pyran derivatives: Investigation of kinetics and mechanism[J]. Chinese Journal of Catalysis, 2015, 36(5): 757-763.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60302-8

https://www.cjcatal.com/EN/Y2015/V36/I5/757

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