Sulfur-based protecting groups for pyrroles and the facile deprotection of 2-(2,4-dinitrobenzene)sulfinyl and sulfonyl pyrroles | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7856562

Reference Type

Journal Article

Title

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

Author(s)

Thompson, A; Butler, RJ; Grundy, MN; Laltoo, AB; Robertson, KN; Cameron, TS

Year

2005

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Volume

Issue

Page Numbers

3753-3756

Language

English

PMID

15845023

DOI

10.1021/jo050077b

Web of Science Id

WOS:000228603200056

Abstract

[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.