Journal of Organic Chemistry p. 206 - 214 (2016)
Update date:2022-08-05
Topics:
Breton, Gary W.
Suroviec, Alice H.
The reaction of N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with anisole in the presence of trifluoroacetic acid affords unexpected disubstituted urazole products instead of the expected monosubstituted urazole as typically observed in the reactions of MeTAD with other substituted benzenes. Our investigation into the mechanism of formation of these disubstituted products suggests that MeTAD is capable of further reaction with the initially formed monosubstituted urazole to afford a persistent urazole radical. The identity of this radical has been established by UV-vis spectroscopy, the nature of its self-dimerization reaction, and via independent generation. Electrochemical oxidation of this radical was carried out, and the resulting diazenium ion was demonstrated to be reactive with added substituted benzenes, including anisole. When oxidation was carried out chemically using thianthrenium perchlorate in the presence of anisole it was shown to produce the same disubstituted products (and in the same ratio) as observed in the acid-catalyzed reaction. A common diazenium species is proposed to be active in both cases. We also report the synthesis and characterization of three interesting tetrazane dimers resulting from unstable urazole radicals.
View MoreContact:+86-575-82733999 0575-82732999
Address:hangzhou gulf fine chemical zone,shangyu city,zhejiang province
Zhongshan Haihong Medicine Co., Ltd.
Contact:86-0760-86925778 (0)18824993998
Address:A7 building,lianyuan road Torch Hi-tech Industrial Development Zone
website:http://www.weichichem.com
Contact:+8613912949432
Address:Fine Chemical Industrial Base,Wujiang town,He County,Anhui China.
website:http://www.shengmaochem.com
Contact:86-27-82853423, 82819281
Address:Rm 202, A Unit Huaqiao Building No. 2, Lihuangpi Road, Wuhan, China
Hubei Xinjing New Material Co.,Ltd
Contact:+86-27-83313147
Address:Room402.#Bthe 7th,Headquarter of Huifeng Corporation Qiaokou District,Wuhan China
Doi:10.1039/b602334g
(2006)Doi:10.1016/j.bmc.2006.05.076
(2006)Doi:10.1039/b606373j
(2006)Doi:10.1016/j.bmcl.2007.02.054
(2007)Doi:10.1016/S0031-9422(00)97490-9
(1976)Doi:10.1016/j.jorganchem.2006.05.032
(2006)