Addition/Correction Cite This: J. Org. Chem. XXXX, XXX, XXX−XXX
pubs.acs.org/joc
Correction to Intrinsically Safe and Shelf-Stable Diazo-Transfer Reagent for Fast Synthesis of Diazo Compounds Ziqiang Yan, Shibo Xie, Yuanheng Li, Qun Song, and Mingming Ma* J. Org. Chem. 2018, 83 (18), 10916−10921. DOI: 10.1021/acs.joc.8b01587
Downloaded by 185.101.71.133 at 05:35:22:371 on May 24, 2019 from https://pubs.acs.org/doi/10.1021/acs.joc.9b00914.
T
he authors wish to correct this article based on two major concerns that have come to our attention. Out of an abundance of caution and with safety foremost in our consideration, we urge all readers of our paper to consider the following points and explanations regarding the original article. First: A more recent work has amended the statements about the safety of ADT. The reagent ADT is not safe in enclosed systems under elevated temperatures. It has a significant risk of runaway exothermic reaction leading to explosion, in common with many other azide reagents. All readers of our paper are urged to consult the paper of Bull et al.: Green, S. P.; Payne, A. D.; Wheelhouse, K. M.; Hallett, J. P.; Miller, P. W.; Bull, J. A. Diazo Transfer Reagent 2-Azido4,6-Dimethoxy-1,3,5-Triazine (ADT) Displays Highly Exothermic Decomposition Comparable to Tosyl Azide. J. Org. Chem. 2019, 84, 5893−5898. DOI: 10.1021/acs.joc.9b00269. Second: Reconsidered interpretation of the DSC data in our work is needed based on the study by Dr. Matsui et al.: Kayama, R.; Hasunuma, S.; Sekiguch.S; Matsui, K. Thermal Reactions of Azido-1,3,5-triazines. Bull. Chem. Soc. Jpn. 1974, 47, 2825−2829. DOI: 10.1246/bcsj.47.2825. We have now realized that the endothermal peak in the range of 130−200 °C in the DSC curve of ADT (Figure 1c) 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. The two endothermal peaks on the DSC trace at 84.7 and 174.2 °C (Figure 1c) correspond to melting and evaporation (not thermal decomposition) of ADT (Figure 1d), respectively. Finally, while the previous study of Matsui et al. 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. noted above 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.
© XXXX American Chemical Society
A
DOI: 10.1021/acs.joc.9b00914 J. Org. Chem. XXXX, XXX, XXX−XXX
