Revisit to the sulfonation of pyrroles: is the sulfonation position correct?

Authors
Mizuno, A Kan, Y Fukami, H Kamei, T Miyazaki, K Matsuki, S Oyama, Y
Citation
A. Mizuno et al., Revisit to the sulfonation of pyrroles: is the sulfonation position correct?, TETRAHEDR L, 41(34), 2000, pp. 6605-6609
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
34
Year of publication
2000
Pages
6605 - 6609
Database
ISI
SICI code
0040-4039(20000819)41:34<6605:RTTSOP>2.0.ZU;2-#
Abstract
Sulfonation of pyrrole and its 1-methyl derivatives with a sulfur trioxide- pyridine complex was found to give 3-sulfonated pyrroles, but not 2-sulfona tes as described in textbooks. The replacement of 1-methyl-2-tri-n-butylsta nnylpyrrole with trimethylsilyl chlorosulfonate, followed by quenching with aq. NaHCO3 also generated sodium 1-methylpyrrole-3-sulfonate, not 2-sulfon ate. (C) 2000 Elsevier Science Ltd. All rights reserved.