Stereoelectronic Effects on Dienophile Separation Influence the Diels–Alder Synthesis of Molecular Clefts

Martin J. Stoermer, Wasantha A. Wickramasinghe, Karl A. Byriel, David C.R. Hockless, Brian W. Skelton, Alexandre N. Sobolev, Allan H. White, Jeffrey Y.W. Mak, David P. Fairlie

Research output: Contribution to journalArticle


The formal cycloaddition adduct of 1,4-benzoquinone with two equivalents of cyclopentadiene is a scaffold with two non-conjugated alkenes. Both alkenes undergo endo [4+2] cycloaddition with a diene to form a rigid U-shaped molecular cleft. Here we show experimental, computational and structural evidence that π interactions between the alkenes affect structural rigidity, Diels–Alder reactivity, cleft formation and host–guest capture.

Original languageEnglish
Pages (from-to)6793-6796
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number45
Publication statusPublished - 8 Dec 2017


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