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Synthesis and characterization of new quaternary ammonium surfactant [C18-Dabco][Br] and its catalytic application in the synthesis of spirocarbocycles under ultrasonic condition

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Abstract

A novel DABCO-based cationic surfactant [C18-Dabco][Br] has been easily synthesized by the reaction of DABCO and octadecyl bromide in acetonitrile at room temperature in excellent yield. The synthesized surfactant was fully characterized by various techniques like FT-IR, 1H NMR, 13C NMR, LC–MS and TGA-DTA analysis. Furthermore, the critical micelle concentration of the surfactant was determined by the conductivity measurement method. The activity of the [C18-Dabco][Br] has been demonstrated for the one-pot synthesis of spirocarbocycles under ultrasonic conditions in water. The presence of the long alkyl chain acts as the hydrophobic part while the free tertiary nitrogen site in the surfactant acts as a base and enhances the overall catalytic activity.

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Acknowledgement

One of the authors, Mr. Trushant Lohar, is very grateful to the Department of Science and Technology (DST), New Delhi, for awarding a DST-INSPIRE Fellowship (IF 140918).

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Authors and Affiliations

  1. Department of Chemistry, Shivaji University, Kolhapur, 416004, Maharashtra, India

    Trushant Lohar, Audumber Patil, Siddharth Kamat & Rajashri Salunkhe

  2. Department of Chemistry, P.D.V.P. College, Tasgaon, Sangli, 416312, Maharashtra, India

    Arjun Kumbhar

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  1. Trushant Lohar
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  2. Arjun Kumbhar
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Correspondence to Rajashri Salunkhe.

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Lohar, T., Kumbhar, A., Patil, A. et al. Synthesis and characterization of new quaternary ammonium surfactant [C18-Dabco][Br] and its catalytic application in the synthesis of spirocarbocycles under ultrasonic condition. Res Chem Intermed 45, 1639–1651 (2019). https://doi.org/10.1007/s11164-018-3690-8

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