Terminally perfluorinated long-chain alkanethiols

This paper describes the synthesis of a series of alkanethiols containing p erfluorinated 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 alky l 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 goo d yields under free radical conditions. Reduction of the resulting secondar y iodides gave long-chain alkanethioacetates with perfluoroalkyl terminal s egments. These intermediates were readily transformed into the correspondin g terminally perfluorinated alkanethiols by acidic deprotection. The produc t thiols should find use in the generation of well-defined fluorinated inte rfaces using the self-assembled monolayer (SAM) technique. (C) 1999 Elsevie r Science S.A. All rights reserved.