Issue 1, 2009
From the journal:

Green Chemistry

Solvent-free Diels–Alder reactions of in situ generated cyclopentadiene†

David Huertas,a   Melinda Florschera  and  Veljko Dragojlovic*a  

* Corresponding authors

a Wilkes Honors College of Florida Atlantic University, 5353 Parkside Drive, Jupiter, FL, USA
E-mail: vdragojl@fau.edu
Fax: 561-799-8602
Tel: 561-799-8012

Abstract

A solvent-free Diels–Alder reaction was carried out by heating a mixture of dicyclopentadiene and a dienophile. Cyclopentadiene, formed in situ, reacted with the dienophile in a thermodynamically controlled reaction. Besides being solvent-free, the described procedure allows for almost complete utilization of dicyclopentadiene and avoids handling of noxious and hazardous cyclopentadiene. The reaction worked well with dienophiles such as maleic anhydride and unsaturated esters. However, unsaturated acids were not suitable dienophiles, yielding Diels–Alder adducts in a low yield.

Graphical abstract: Solvent-free Diels–Alder reactions of in situ generated cyclopentadiene

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Article information

DOI
https://doi.org/10.1039/B813485E
Article type
Paper
Submitted
04 Aug 2008
Accepted
10 Oct 2008
First published
07 Nov 2008

Green Chem., 2009,11, 91-95

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Solvent-free Diels–Alder reactions of in situ generated cyclopentadiene

D. Huertas, M. Florscher and V. Dragojlovic, Green Chem., 2009, 11, 91 DOI: 10.1039/B813485E

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