Preparation of Oligo(ethylene glycol)-Terminated Icosanedisulfides

Thomas D. Clark; Elizabeth C. Dugan

doi:10.1055/s-2006-926377

PAPER

Preparation of Oligo(ethylene glycol)-Terminated Icosanedisulfides

Thomas D. Clark*, Elizabeth C. Dugan
Naval Research Laboratory, Division of Chemistry, Washington, DC 20375-5342, USA
Fax: +1(202)7673321; e-Mail: thomas.clark@nrl.navy.mil;

Abstract

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Abstract

This paper describes the synthesis of hexa(ethylene glycol) and carboxymethylhexa(ethylene glycol)-terminated alkanedisulfides 4 and 7, respectively, in which the alkylene chains are twenty-methylenes-long. The key twenty-carbon synthon, 20-bromoicos-1-ene (1), was prepared by homologation of 8-bromooct-1-ene, which was achieved via Cu(II)-catalyzed coupling of the corresponding Grignard reagent with 1,12-dibromododecane. Compounds 4 and 7 are expected to yield self-assembled monolayers (SAMs) that are more stable and well-ordered than those formed by their traditional undecane homologues.

Key words

Grignard reaction - oligo(ethylene glycol) - thiols - carboxylic acids - self-assembled monolayers

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References

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