Microwave Induced Preparations of Incipient and Solvent Stabilized Cyclopentadiene for Diels-Alder Reactions with Kinetic Control

Author(s): J. Michael Robinson, Kristina A. Chang, Chelsey C. Gorter, Mary E. Kincade, Ashley N. Pinson, Marisa P. Ramos, Rachel F. Ramos, Mark D. Reno, Christopher J. Valenzuela, Tatiana Vidal, Marcus W. Worden, Virginia R. Zamudio

Journal Name: Current Microwave Chemistry

Volume 2 , Issue 2 , 2015

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Graphical Abstract:


A microwave induced reaction of dicyclopentadiene (1) was used to rapidly and conveniently generate cyclopentadiene (2) which is stabilized in a polar solvent for subsequent use. In this case 2 was used for Diels-Alder reactions at ambient temperature. A 3 min microwave induced reaction of 1 in acetone gave a solution of 2, followed by a room temperature reaction with a limited amount of a highly active dienophile, maleic anhydride (3), which afforded pure cis-endo-5- norbornene-2,3-dicarboxilic anhydride (4). Simultaneous reactions were achieved in 0.5 min at 200°C but some of the exo-isomer 5 also resulted. Several maleimides also demonstrated the convenient utility of these microwave methods for reactions of 2 for valuable industrial compounds. This method now precludes the previous arduous thermal cracking of 1 along with the simultaneous fractional distillation of 2.

Keywords: 1H NMR, acetone, biotage Initiator +, cis-endo-5-norbornene-2, 3-dicarboxylic anhydride, cis-exo-5-norbornene- 2, 3-dicarboxylic anhydride, cyclopentadiene, dicyclopentadiene, Diels-Alder, maleic anhydride, maleimide, microwave, Nmethylmaleimide, N-phenylmaleimide, reaction severity, solvent stabilization.

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Article Details

Year: 2015
Page: [136 - 143]
Pages: 8
DOI: 10.2174/2213335601666141202235427
Price: $25

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