Structural Studies on Cycloadducts of Furan, 2-Methoxyfuran, and 5-Trimethylsilylcyclopentadiene with Maleic Anhydride and N-Methylmaleimide

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• 作者：Yit Wooi Goh ; Brett R. Pool ; Jonathan M. White
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：January 4, 2008
• 年：2008
• 卷：73
• 期：1
• 页码：151 - 156
• 全文大小：157K
• 年卷期：v.73,no.1(January 4, 2008)
• ISSN：1520-6904

文摘

The early stages of the retro-Diels-Alder reaction are clearly apparent in the structures of the cycloadductsformed between furan or 5-trimethylsilylcyclopentadiene with maleic anhydride and N-methylmaleimide.The degree of lengthening of the C-C bonds that break in this reaction is clearly related to the knownreactivity of these cycloadducts toward this reaction. In the structures of the cycloadducts 21 and 22derived from 2-methoxyfuran, the early stages of an alternative fragmentation reaction are apparent,consistent with the reactivity of these compounds in solution.