4.8 Article

Zemplen transesterification: a name reaction that has misled us for 90 years

Journal

GREEN CHEMISTRY
Volume 17, Issue 3, Pages 1390-1394

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4gc02006e

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Funding

  1. National Natural Science Foundation of China [21272083]

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We demonstrated that using NaOH and NaOMe in methanol for deacylation are identical, indicating that the Zemplen condition has been misleading us for almost 90 years. The traditional base-catalyzed mechanism cannot be used to explain our results. We propose that H-bond complexes play key roles in the base-catalyzed process, explaining why deacylation in methanol can be catalyzed by hydroxide.

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