The reaction of acyl cyanides with “Huisgen zwitterion”: an interesting rearrangement involving ester group migration between oxygen and nitrogen atoms

Xu-Guang Liu; Yin Wei; Min Shi

doi:10.1039/B913196E

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Organic & Biomolecular Chemistry

Issue 22, 2009

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The reaction of acyl cyanides with “Huisgen zwitterion”: an interesting rearrangement involving ester group migration between oxygen and nitrogen atoms

Xu-Guang Liu , Yin Wei and Min Shi

Org. Biomol. Chem., 2009, 7, 4708-4714

DOI: 10.1039/B913196E
Received 02 Jul 2009, Accepted 24 Aug 2009
First published on the web 17 Sep 2009

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A novel rearrangement involving ester group migration was found in the reaction of acyl cyanides and Huisgen zwitterions, affording hydrazone derivatives at higher temperature (90 °C) and azine derivatives at lower temperature (20 °C), respectively. Interestingly, the reaction temperature is identified as a critical factor to control the final products. Presumably, the rearrangement involving ester group migration between oxygen and nitrogen atoms leads to the formation of different products.

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Organic & Biomolecular Chemistry

The reaction of acyl cyanides with “Huisgen zwitterion”: an interesting rearrangement involving ester group migration between oxygen and nitrogen atoms

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