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Sulfur-Based Protecting Groups for Pyrroles and the Facile Deprotection of 2-(2,4-Dinitrobenzene)sulfinyl and Sulfonyl Pyrroles

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journal contribution
posted on 29.04.2005 by Alison Thompson, R. Jonathan Butler, Meaghan N. Grundy, Andrea B. E. Laltoo, Katherine N. Robertson, T. Stanley Cameron
The effectiveness of simple sulfinyl and sulfonyl groups as electron-withdrawing protecting groups for pyrroles has been analyzed using 13C NMR spectroscopy and confirmed by consideration of X-ray crystal structures. Additionally, the 2,4-dinitrobenzenesulfinyl and sulfonyl groups are shown to be effective electron-withdrawing protecting groups for pyrroles, and they can be removed by treatment with benzene thiol or thiolate under mild and specific conditions.