Synthesis 2005(15): 2527-2532  
DOI: 10.1055/s-2005-872106
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel 8-Oxotheaspiranes and Dihydro Analogues Possessing a Partly Fluorinated Ring

Claire Amato*a, Julien Reboula, Jean-Pierre Finetb, Patrick Calasa
a UMR 5073 - OMEMF, cc 017, Université de Montpellier II, Sciences et Techniques du Languedoc, Place Eugène Bataillon, 34095 Montpellier Cedex 05, France
Fax: +33(4)67631046; e-Mail: c.amato@univ-montp2.fr;
b UMR 6517 - CBRL, cc 521, Université de Provence, Faculté des Sciences Saint-Jérôme, Av. Esc. Normandie - Niemen, 13397 Marseille Cedex 20, France
Further Information

Publication History

Received 14 March 2005
Publication Date:
29 July 2005 (online)

Abstract

New spiro compounds, 8-oxotheaspiranes analogues and dihydro equivalents possessing a partly fluorinated ring, are obtained from 5-(ω-iodoperfluoropropyl)furan-3(2H)-one and unsaturated compounds through an annulation process (favored 6-exo-trig). Yields observed appear as largely depending on the nature of the unsaturated substrate used. For primary alkynols or alkenols or allyl oxycoumarin, the annulation process largely predominates over the radical chain addition process. The contrary is observed when the alkynols or alkenols used are tertiary ones.

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15

Crystallographic data (excluding structure factors) for this structure have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC-265643. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44 1223/336033 or e-mail: deposit@ccdc.cam.ac.uk).