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Royal Society of Chemistry, Chemical Communications, 3(50), p. 353-355, 2014

DOI: 10.1039/c3cc46828c

Wiley-VCH Verlag, ChemInform, 13(45), p. no-no, 2014

DOI: 10.1002/chin.201413112

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From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual SNAr via thiolate displacement?

Journal article published in 2014 by Aoife A. Ryan, Shane Plunkett, Aoife Casey, Thomas McCabe, Mathias O. Senge ORCID
This paper is available in a repository.
This paper is available in a repository.

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Abstract

Treatment of meso 2-ethylhexyl-3-mercaptopropionate substituted porphyrins with base at room temperature generated a porphyrin thiolate anion which in situ reacted in a nucleophilic aromatic substitution (SNAr) reaction with remaining thioether derivative. This reaction yielded S-linked bisporphyrins in good yields, with mechanistic insight obtained via displacement reactions. Additionally, SNAr of the thioether chain was achieved using S- and organolithium nucleophiles.