Oligomerization of 1,2-ethanedithiol: An expedient approach to oligothiaethylenethioglycols

Dvora Berkovich-Berger, N. Gabriel Lemcoff, Sarah Abramson, Mikhail Grabarnik, Sarah Weinman, Benzion Fuchs

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Reactions of ethylenedithioglycol (ETG) with Na2CO3, K2CO3, and Cs2CO3 provided the oligothiaethylenethioglycols (nETG): di(DETG), tri- (TrETG), tetra- (TETG), and pentathiaethylenethioglycol (PETG), along with higher polymers. The most efficient carbonate was K2CO3 and reactions using DETG and TrETG as starting materials-or their mixtures-were also found to afford similar species. This largely unknown oligomerization process was thoroughly explored and potential pathways were put forward. A convenient conversion of ETG to laboratory quantities of the otherwise scarce and/or expensive DETG, TrETG, TETG, and PETG oligomers, in organic or aqueous media was achieved. Notably, this straightforward reaction takes place without the addition of expensive or toxic metal catalysts and with pure water as the solvent, thereby highlighting its potential as a green chemical reaction. Moreover, the process opens up new approaches to dynamic combinatorial libraries (DCLs) of oligomers and macrocycles with manifolded nETG [(SCH2CH2)nS] bridges.

Original languageEnglish
Pages (from-to)6365-6373
Number of pages9
JournalChemistry - A European Journal
Volume16
Issue number21
DOIs
StatePublished - 1 Jun 2010

Keywords

  • Ethylenedithioglycol
  • Green chemistry
  • Macrocycles
  • Microwave chemistry
  • Oligomerization

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