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

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

References

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7

http://www.fluorous.com.

9

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

20

Ivanko, P.; Takács, F. T.; Rábai, J. Abstracts of Papers, 14th European Symposium on Fluorine Chemistry, Poznan, Poland, 2004; Abstract 84.