Issue 22, 2009
From the journal:

Organic & Biomolecular Chemistry

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

Xu-Guang Liu,a   Yin Wei*b  and  Min Shi*ab  

* Corresponding authors

a School of Chemistry & Molecular Engineering, East China University of Science and Technology130 Mei Long Road, Shanghai, China
Fax: 86-21-64166128

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China
E-mail: weiyin@mail.sioc.ac.cn, Mshi@mail.sioc.ac.cn

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/B913196E
Article type
Paper
Submitted
02 Jul 2009
Accepted
24 Aug 2009
First published
17 Sep 2009

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

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

X. Liu, Y. Wei and M. Shi, Org. Biomol. Chem., 2009, 7, 4708 DOI: 10.1039/B913196E

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