jo050077b_si_001.pdf (208.01 kB)
Sulfur-Based Protecting Groups for Pyrroles and the Facile Deprotection of 2-(2,4-Dinitrobenzene)sulfinyl and Sulfonyl Pyrroles
journal contribution
posted on 2005-04-29, 00:00 authored by Alison Thompson, R. Jonathan Butler, Meaghan N. Grundy, Andrea B. E. Laltoo, Katherine N. Robertson, T. Stanley CameronThe 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.