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

被引：2

作者：

Robinson, J. Michael ^{[1
]}

Chang, Kristina A. ^{[1
]}

Gorter, Chelsey C. ^{[1
]}

Kincade, Mary E. ^{[1
]}

Pinson, Ashley N. ^{[1
]}

Ramos, Marisa P. ^{[1
]}

Ramos, Rachel F. ^{[1
]}

Reno, Mark D. ^{[1
]}

Valenzuela, Christopher J. ^{[1
]}

Vidal, Tatiana ^{[1
]}

Worden, Marcus W. ^{[1
]}

Zamudio, Virginia R. ^{[1
]}

机构：

[1] Univ Texas Permian Basin, Dept Chem, 4901 E Univ Blvd, Odessa, TX 79762 USA

来源：

CURRENT MICROWAVE CHEMISTRY | 2015年 / 2卷 / 02期

关键词：

H-1; NMR; acetone; biotage Initiator +; cis-endo-5-norbornene-2,3-dicarboxylic anhydride; cis-exo-5-norbornene2,3-dicarboxylic; anhydride; cyclopentadiene; dicyclopentadiene; Diels-Alder; maleic anhydride; maleimide; microwave; Nmethylmaleimide; N-phenylmaleimide; reaction severity; solvent stabilization;

D O I：

10.2174/2213335601666141202235427

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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-5norbornene-2,3-dicarboxilic anhydride (4). Simultaneous reactions were achieved in 0.5 min at 200 degrees 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.

引用

页码：136 / 143

页数：8

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