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

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.

Key words

idoperfluoropropylfuranone - 8-oxotheaspiranes - dihydro-8-oxotheaspiranes - annulations - spiro compounds

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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: [phone] or e-mail: [e-mail]).