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

✍ Scribed by Akira Mizuno; Yukiko Kan; Harukazu Fukami; Tomoe Kamei; Kazuo Miyazaki; Shinsuke Matsuki; Yoshiaki Oyama

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
174 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

Sulfonation of pyrrole and its 1-methyl derivatives with a sulfur trioxide±pyridine complex was found to give 3-sulfonated pyrroles, but not 2-sulfonates as described in textbooks. The replacement of 1-methyl-2tri-n-butylstannylpyrrole with trimethylsilyl chlorosulfonate, followed by quenching with aq. NaHCO 3 also generated sodium 1-methylpyrrole-3-sulfonate, not 2-sulfonate.

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