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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, 00:00 authored 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.