Sulfur-based protecting groups for pyrroles and the facile deprotection of 2-(2,4-dinitrobenzene)sulfinyl and sulfonyl pyrroles.
[reaction: see text] The effectiveness of simple sulfinyl and sulfonyl groups as electron-withdrawing protecting groups for pyrroles has been analyzed using (13)C 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.
Thompson
Alison
A
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4J3, Canada alison.thompson@dal.ca
Butler
R Jonathan
RJ
Grundy
Meaghan N
MN
Laltoo
Andrea B E
AB
Robertson
Katherine N
KN
Cameron
T Stanley
TS