Synthesis of 3-perfluoroalkyl-propyl esters of L-(+)-tartaric acid

被引：16

作者：

Szlávik, Z

Tárkányi, G

Tarczay, G

Gömöry, A

Rábai, J

机构：

[1] Eotvos Lorand Univ, Dept Organ Chem, H-1518 Budapest 112, Hungary

[2] Eotvos Lorand Univ, Dept Gen & Inorgan Chem, H-1518 Budapest 112, Hungary

[3] Chem Works Gedeon Richter Ltd, Spectroscop Res Div, Budapest, Hungary

[4] Hungarian Acad Sci, Inst Chem, Chem Res Ctr, H-1525 Budapest, Hungary

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1999年 / 98卷 / 02期

基金：

匈牙利科学研究基金会;

关键词：

perfluoroalkyl-propanols preparation; reduction; fluorinated esters of L-tartaric acid; preparation; esterification; fluorophilicity; gas chromatography;

D O I：

10.1016/S0022-1139(99)00061-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A convenient and effective method for the preparation of perfluoroalkyl-propanols (F(CF2)(n)-(CH2)(3)-OH, n = 6,8,10) via boric acid esters is described. The radical addition of F-alkyl iodides to the C=C double bonds of triallyl berate is followed by the reduction step using tributylstannane hydride under one-pot conditions. Finally, the mild aqueous deprotection of the alcoholic function completes the reaction with an overall yield of 75-79%. The fluorophilicity (f) values of these and some other fluoroalcohols, which describe their phase preference, were determined by gas chromatography. F-alkyl-propanols are useful synthetic precursors of fluorinated esters of L-tartaric acid-potential chelating agents in fluorous biphase transformations. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：83 / 87

页数：5

共 25 条

[1] Additions of PH3 to monosubstituted alkenes of the formula H2C=CH(CH2)x(CF2)yCF3:: Convenient, multigram syntheses of a family of partially fluorinated trialkylphosphines with modulated electronic properties and fluorous phase affinities [J].