ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Micellar effects on kinetics and mechanism of Vilsmeier–Haack formylation and acetylation with Pyridines

Tasneem Mohammed, Aejaz Abdullatif Khan, S. M. Shakeel Iqubal, and Bandar A. Alyami

Department of General Science, Ibn Sina National College for Medical Studies, Jeddah, Kingdom of Saudi Arabia

E-mail: shakeeliqubal@gmail.com

Received: 25 August 2021  Accepted: 5 January 2022

Abstract:

An efficient preparation of Vilsmeier–Haack formylated and acetylated derivatives with pyridine and substituted pyridines has been developed by employing micelles as catalyst. Their kinetic study reveals a phenomenal rate enhancement in anionic SDS, cationic CTAB, and nonionic TX-100 micellar media. The Vilsmeier–Haack reaction follows second order kinetics. Piszkiewicz’s co-operativity model was used to interpret the results in micellar media. The observed activation parameters ΔH and ΔS values were calculated from Eyring’s plots. The main features of this study were easy process, mild reaction conditions and readily available reagents.

Graphical abstract

Keywords: Acetylation; Formylation; Micelles; Pyridine; Vilsmeier; Haack reaction

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02066-7

Chemical Papers 76 (5) 2615–2621 (2022)