Intrinsically Safe and Shelf-Stable Diazo-Transfer Reagent for Fast Synthesis of Diazo Compounds
Shibo Xie, Ziqiang Yan, Yuanheng Li, Qun Song, Mingming Ma*
*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China,
Email: mma
ustc.edu.cn
S. Xie, Z. Yan, Y. Li, Q. Song, M. Ma, J. Org. Chem., 2018, 83, 10916-10921.
DOI: 10.1021/acs.joc.8b01587
see article for more reactions
Abstract
2-Azido-4,6-dimethoxy-1,3,5-triazine (ADT) as an intrinsically safe, highly efficient, and shelf-stable diazo-transfer reagent. ADT is very stable upon >1 year storage under air at room temperature. Diazo-transfer reactions based on ADT give diazo compounds in excellent yields within several minutes at room temperature.
see article for more examples
While ads financed 62% of the published abstracts in 2024, donations allowed us to publish additional 12%. 26% of the abstracts have been published voluntarly. If you kindly donate, we can publish more freely accessible information and help the chemical community even more:
If you don't like pawalls or a flood of more and more advertising, then you can send a clear signal here!
Note
The endothermal peak in the range of 130-200°C in the DSC curve of ADT is mainly due to the endothermal evaporation of ADT, not due to the decomposition of ADT. Therefore, the "endothermal decomposition of ADT" was a mistaken interpretation of this endothermal peak in the DSC curve. While a previous study of Matsui et al. (Bull. Chem. Soc. Jpn. 1974, 47, 2825-2829.) had demonstrated the thermal stability of ADT up to 180°C, the updated interpretation of the DSC data and the recent findings of Bull et al. (J. Org. Chem. 2019, 84, 5893-5898.) suggest that while ADT may be employed safely under various conditions and operating procedures, it is essential that care should be taken to ensure safe practices as is always the case in reactions of azide compounds.
Mingming Ma, May 23, 2019
Key Words
ID: J42-Y2018
