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Synthesis 2002(18): 2711-2716
DOI: 10.1055/s-2002-35986
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© Georg Thieme Verlag Stuttgart · New York

Rearrangement of Allyl Aryl Ethers; Part V: [1] Reaction of 2,5-Dialkoxyhydroquinone with Cycloalkanediols

Olivér Orovecza, Péter Kovácsb, Pál Kolonitsa, László Párkányib, Éva Szabóc, Lajos Novák*a
a Institute for Organic Chemistry, Budapest University of Technology and Economics, 1111 Budapest, Gellért tér 4, Hungary
Fax: +36(1)4633297; e-Mail: lnovak@mail.bme.hu;
b Central Research Institute of Chemistry, 1525, Budapest, P.O. Box 17, Hungary
c EGIS Pharmaceuticals Ltd., 1475, Budapest 10, P.O. Box 100, Hungary
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Publication History

Received 19 September 2002
Publication Date:
06 December 2002 (online)

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Abstract

Benzo[1,4]dioxines 5 and 6 were prepared in a one pot reaction from 2,5-dialkoxy-hydroquinone 1 and cycloalkane-1,2-diol 2. Acid-catalyzed reaction of 1 and 2 yielded a mixture of cycloalkanobenzofuran 11 and spiro compound 12. The mechanisms of these novel reactions are also discussed.

Key words

rearrangements - nucleophilic aromatic substitutions - dioxines - furans - spiro compounds - ethers