Mechanistic Insights into the Stepwise Diels鈥揂lder Reaction of 4,6-Dinitrobenzofuroxan

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• 作者：Mats Linder ; Adam Johannes Johansson ; Tore Brinck
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：January 6, 2012
• 年：2012
• 卷：14
• 期：1
• 页码：118-121
• 全文大小：749K
• 年卷期：v.14,no.1(January 6, 2012)
• ISSN：1523-7052

文摘

The stepwise Diels鈥揂lder reaction between 1-trimethylsiloxy-1,3-butadiene and 4,6-dinitrobenzofuroxan is explored using state-of-the-art computational methods. The results support a stepwise mechanism via a persistent intermediate, however, not the one previously reported (Lakhdar et al., Chem. Eur. J.2007, 16, 5681) but a heterocyclic adduct. The novel DFT functional M062X and the SCS-MP2 method were essential to reproduce a reasonable potential energy surface for this challenging system.