From thioether substituted porphyrins to sulfur linked porphyrin dimers: An unusual SNAr via thiolate displacement?
Item Type:Journal Article
Citation:Ryan, A.A., Plunkett, S., Casey, A., McCabe, T., Senge, M.O., From thioether substituted porphyrins to sulfur linked porphyrin dimers: An unusual SNAr via thiolate displacement?, Chemical Communications, 50, 3, 2014, 353-355
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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.
Type of material:Journal Article
Series/Report no:Chemical Communications
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