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Synthesis 2007(16): 2581-2584  
DOI: 10.1055/s-2007-983779
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© Georg Thieme Verlag Stuttgart · New York

3-(Perfluoroalkyl)propanols: Valuable Building Blocks for Fluorous Chemistry

József Rábai*, Csongor Szíjjártó, Peter Ivanko, Dénes Szabó
Department of Organic Chemistry, Institute of Chemistry, Eötvös Loránd University, P. O. Box 32, 1518 Budapest 112, Hungary
Fax: +36(1)3722592; e-Mail: rabai@elte.hu;
Further Information

Publication History

Received 26 February 2007
Publication Date:
12 July 2007 (online)

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Abstract

2-Iodo-3-(perfluoroalkyl)propanols are obtained in excellent yields and several-hundred-gram quantities by the controlled radical addition of commercially available n-perfluoroalkyl and perfluoroisoalkyl iodides to allyl alcohol. Their consecutive reduction with hydrazine hydrate and Raney nickel catalyst in methanol afforded the corresponding 3-(perfluoroalkyl)propanols in high yields and purity.

Key words

alkyl halides - alcohols - fluorine - reductive dehalogenation - transfer hydrogenation

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http://www.fluorous.com.

9

FTI Catalogue (2006) lists RFn(CH2)3OH at $32, $35, $100, and $35 for 2 g each of n = 4, 6, 7, and 8, respectively.

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