Mitsunobu synthesis of symmetrical alkyl and polyfluoroalkyl secondary amines

被引：20

作者：

Bálint, AM

Bodor, A

Gömöry, A

Vékey, K

Szabó, D

Rábai, J

机构：

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

[2] Eotvos Lorand Univ, Dept Theoret Chem, H-1518 Budapest, Hungary

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

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2005年 / 126卷 / 11-12期

基金：

匈牙利科学研究基金会;

关键词：

amines; fluorophilicity; ideal separation; Mitsunobu reaction; trifluoromethanesulfonamide;

D O I：

10.1016/j.jfluchem.2005.08.012

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Trifluoromethanesulfonamides (triflamides) having the structure CF3SO2N[(CH2)(3)R](2) (R = CnF2n+1 or CnH2n+1, n = 4, 6, 8, 10) are obtained in high yields, when CF3SO2NH2 is reacted with 3-perfluoroalkyl-1-propanols or the parent aliphatic alcohols in a Mitsunobu reaction (Ph3P/[i-PrO2CN=NCO2-i-Pr]/ether). Products are isolated easily by fluorous extraction, fluorous solid-organic liquid filtration or n-heptane/CH3OH extraction. Consecutive deprotection of triflamides with LiAlH4 in boiling ether or dioxane solution affords the title amines in good overall yields. Fluorous partition coefficients of the F-tagged amides and amines are determined and qualitatively analyzed. (c) 2005 Elsevier B.V. All rights reserved.

引用

页码：1524 / 1530

页数：7

共 41 条

[1] Improved synthesis of perfluorooctylpropyl amine [J].