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

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

1.
Department of Chemistry, University of Sistan and Baluchestan, Zahedan, Iran

Corresponding author: Sayyed Mostafa Habibi-Khorassani,
Received Date: 16 December 2014
Available Online: 19 January 2015

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.
- Fructose,
- Catalyst,
- Kinetics,
- Mechanism,
- Tetrahydrobenzo[b]pyran derivative
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沈阳化工大学材料科学与工程学院沈阳 110142