Sulfur-based protecting groups for pyrroles and the facile deprotection of 2-(2, 4-dinitrobenzene) sulfinyl and sulfonyl pyrroles

…, ABE Laltoo, KN Robertson, TS Cameron

Index: Thompson, Alison; Butler, R. Jonathan; Grundy, Meaghan N.; Laltoo, Andrea B. E.; Robertson, Katherine N.; Cameron, T. Stanley Journal of Organic Chemistry, 2005 , vol. 70, # 9 p. 3753 - 3756

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Citation Number: 22

Abstract

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 ...