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AASCIT Journal of Chemistry

2015; 2(2): 43-47

Published online April 10, 2015 (


Diels-Alder Reaction, Ionic Liquid,

Solid Supports, Microwave,


Received: March 19, 2015 Revised: March 30, 2015 Accepted: March 31, 2015

Highly Efficient Green Diels-Alder Reaction Between Isoprene and 2-Cyclopentene-1-One Under Microwave Irradiation

Annamalai Rajendran1, *, Ganesan Vinoth Kumar2

1Department of Chemistry, Sir Theagaraya College, Chennai-21, India

2Research and Development Centre, Bharathiar University, Coimbatore-46, India

Email address (A. Rajendran)


Annamalai Rajendran, Ganesan Vinoth Kumar. Highly Efficient Green Diels-Alder Reaction Between Isoprene and 2-Cyclopentene-1-One Under Microwave Irradiation. AASCIT Journal of Chemistry. Vol. 2, No. 2, 2015, pp. 43-47.


A solid supported synthetic technique has been established for the Diels-Alder reaction between isoprene and 2-cyclopentene-1-one using solid supports as energy transfer medium under microwave irradiation in 3-methyl-1-octyl-imidazolium tetrachloroaluminate ionic liquid. The experimental results obtained by microwave irradiation technique were compared with those attained by the conventional method. This solvent-free technique coupled with the excellent yields and short reaction time makes this procedure environmentally benign for synthesis.

1. Introduction

The stress-free way of synthesizing a six membered cyclic compound is applying Diels-Alder reaction, known as one of the examples of pericyclic reactions, between a conjugated diene and a dienophile to form a substituted cyclohexene adduct [1]. Conventional synthetic methods of consuming massive volumes of organic solvents for the preparation of organic compounds have been creating pollution issue and global warming around the globe. These drawbacks make ionic liquids as smart substitute to the conventional synthesis processes. The suitable and essential alternative to initiate the construction of pollution less environment was green processing. In recent years various techniques such as mixers, microreactors, spin disc reactor, oscillated flow reactors, microwave irradiation, ultrasonication, multifunctional membranes and coiled flow inverter have been applied for the green synthetic processes [2]. Although various techniques are available for green synthesis, microwave irradiation technique was selected for the present work up of Diels-Alder reaction between isoprene and 2- cyclopentene-1-one at various reaction conditions. The main features of utilizing this microwave technology are performing at easy work-up conditions, setting up and monitoring of reaction temperature, pressure, reaction time, rapid reaction rates and excellent yields [3]. Due to these benefits microwave techniques have widely been used already for the synthesis of number of compounds [4, 5].

In addition to microwave technology, solid supports such as LiNTf2, Y(OTf)3, Sc(OTf)3, etc. have also played outstanding performance in acceleration of several Diels-Alder reactions conducted in ionic liquids. The use of these type of solid supports is essential for a smooth reaction [6]. In this presently reported experiments, 3-methyl-1- octyl-imidazolium tetrachloroaluminate ionic liquid was selected as reaction medium as it has excellent activity than imidazolium based tetrafluoroborate ionic

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