Regio- and Stereoselective Addition of Perfluoroalkyl Iodides to Allenes Conjugated with Carbon-Oxygen or Phosphorus-Oxygen Double Bonds

Abstract

In the presence of sodium dithionite, allenes conjugated with a carbon-oxygen or a phosphorus-oxygen double bond, such as allenic phosphonates, phosphine oxides and allenecarboxylates, reacted readily with perfluoroalkyl iodides at room temperature to give the corresponding addition products in moderate yields with complete regioselectivity and stereoselectivity. Perfluoroalkyl groups were introduced into the terminal position of allenes and addition products with the E-configuration were obtained selectively by the reaction.

Key words

perfluoroalkyl iodides - allenes - radical addition - stereo­selectivity - regioselectivity

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7

The crystal structure of 3a has been deposited as supplementary publication No. CCDC-619205 at the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to: CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; e-mail: [e-mail] or
http//www.ccdc.cam.ac.uk.