Arene 1,4-Diradical Formation from o-Dialkynylarenes

M. F. Semmelhack, Thomas Neu, Francisco Foubelo

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A series of 10-membered cyclic 1,5-diynes has been prepared with arene rings fused at positions C-3/C-4. The arenes include simple benzene rings, a naphthoquinone and naphthohydroquinone, and an anthraquinone and anthracene unit. Consistent with a simple picture relating the extent of double bond character in the ene part of the ene-diyne with the rate of arene-1,4-diyl formation, the hydroquinone derivatives were much less reactive compared to the corresponding quinones. Substituents such as propargylic hydroxyl or keto group have a small but significant activating effect. The parent 3,4-benzo-1,8-decadiyne shows a half-life for rearrangement of 24 h at 84 °C while the corresponding alkene, cyclodec-3-ene-1,5-diyne is reported to have a half-life of 18 h at 37 °C.

Original languageEnglish (US)
Pages (from-to)5038-5047
Number of pages10
JournalJournal of Organic Chemistry
Issue number17
StatePublished - Aug 1 1994

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


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