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Synthesis 2000; 2000(6): 809-812
DOI: 10.1055/s-2000-6278
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Rearrangement of Allyl Aryl Ethers; IV: Reaction of Trimethylhydroquinone with Cycloalkanediols

Lajos Novák* , Péter Kovács, Pál Kolonits, Olivér Orovecz, Jenő Fekete, Csaba Szántay
  • *Institute for Organic Chemistry, Budapest University of Technology and Economics, H-1111 Budapest, Gellért tér 4, Hungary; Fax +36 (1) 4 63 32 97; E-mail: l-novak.szk@chem.bme.hu
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Publication Date:
31 December 2000 (online)

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Cycloalkanobenzofurans 3a-d were prepared in a one-pot reaction from trimethylhydroquinone (1) with cycloalka-1,3-dienes 2a-d. Acid-catalyzed reaction of 1 and cycloalkane-1,2-diols 4c-h afforded spiro compounds 6a-c. The mechanism of these novel ring-contraction reactions is also discussed.

rearrangements - ring contraction - benzofurans - spiro compounds - diols - quinones - cyclizations