Terminally perfluorinated long-chain alkanethiols

被引：58

作者：

Graupe, M ^{[1
]}

Koini, T ^{[1
]}

Wang, VY ^{[1
]}

Nassif, GM ^{[1
]}

Colorado, R ^{[1
]}

Villazana, RJ ^{[1
]}

Dong, H ^{[1
]}

Miura, YF ^{[1
]}

Shmakova, OE ^{[1
]}

Lee, TR ^{[1
]}

机构：

[1] Univ Houston, Dept Chem, Houston, TX 77204 USA

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1999年 / 93卷 / 02期

基金：

奥地利科学基金会; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0022-1139(98)00284-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

This paper describes the synthesis of a series of alkanethiols containing perfluorinated terminal segments: F(CF2)(m)(CH2)(n)SH, where m = I, n = 9-15; m = 2, n = 11-14; m = 3, n = 10-13; and m = 4, n = 9-12. Fluorinated alkyl iodides of the general formula F(CF2)(m)(CH2)(n)I, where m = 1-4 and n = 0 or 1, were added to long-chain omega-olefins that were functionalized at the alpha-terminus with a thioacetate group. The reactions proceeded in good yields under free radical conditions. Reduction of the resulting secondary iodides gave long-chain alkanethioacetates with perfluoroalkyl terminal segments. These intermediates were readily transformed into the corresponding terminally perfluorinated alkanethiols by acidic deprotection. The product thiols should find use in the generation of well-defined fluorinated interfaces using the self-assembled monolayer (SAM) technique. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：107 / 115

页数：9

共 33 条

[1] SYNTHESIS OF FLUORINATED ACETYLENES [J].