A Method
for Heteroaromatic Nitration Demonstrating
Remarkable Thermal Stability

Eastgate, Martin D.

A Method for Heteroaromatic Nitration Demonstrating Remarkable Thermal Stability

Posted on 2014-12-19 - 00:00

Herein we report a novel heterogeneous pyrrole nitration that can be run on a large scale in batch mode. Activation of sodium nitrate by SO₃–pyridine in acetonitrile leads to the formation of an insoluble nitronium sulfate intermediate that effects a high-yielding reaction. These conditions allow for a safer and practical nitration reaction with unique thermal stability that appears to be a function of the low solubility of the proposed nitronium ion carrier. Mechanistic insights gained from reaction kinetics as well as ¹H and ¹⁵N NMR studies are presented to support this analysis.

CITE THIS COLLECTION

Beutner, Gregory L.; Desai, Lopa; Fanfair, Dayne; Lobben, Paul; Anderson, Eric; Leung, Simon W.; et al. (2016). A Method for Heteroaromatic Nitration Demonstrating Remarkable Thermal Stability. ACS Publications. Collection. https://doi.org/10.1021/op5001572

https://doi.org/10.1021/op5001572

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