99233-27-9Relevant academic research and scientific papers
Transition-metal-free mono- or dinitration of protected anilines
Dai, Enrui,Dong, Ying,Dong, Yongrui,Kong, Rui,Liang, Deqiang,Liu, Guangzhang,Ma, Yinhai,Wu, Qiong
, (2020/04/27)
An amide-assisted arene nitration is presented, and both mono- and dinitration of protected anilines could be effected by using NaNO2 and NaNO3 as the mono- and bisnitrating agents, respectively. This divergent synthesis is transition-metal- and acid-free, and features a broad substrate scope, low cost, and ortho–para selectivity.
Ozone-mediated Reaction of Anilides and Phenyl Esters with Nitrogen Dioxide: Enhanced Ortho-reactivity and Mechanistic Implications
Suzuki, Hitomi,Tatsumi, Atsuo,Ishibashi, Taro,Mori, Tadashi
, p. 339 - 344 (2007/10/02)
In the presence of ozone, anilides 1 can be nitrated rapidly with nitrogen dioxide in chloroform at 0 deg C to give a high proportion of ortho-nitro derivatives (ortho:para = 1.2-4.4) in good yields.The phenyl esters 15 can be similarly nitrated on the aromatic ring without significant cleavage of the ester bond, giving a mixture of isomeric nitro derivatives in which the ortho-isomer predominantes (ortho:para = 1.1-1.5).The oridin of the enhanced ortho reactivity is discussed in terms of an electron-transfer process involving the nitrogen trioxide as initial electrophile.
Ortho-Selective Nitration of Acetanilides with Nitrogen Dioxide in the Presence of Ozone
Suzuki, Hitomi,Ishibashi, Taro,Murashima, Takashi,Tsukamoto, Kenkichi
, p. 6591 - 6594 (2007/10/02)
In the presence of ozone, nitrogen dioxide rapidly reacts with acetanilides ortho-selectively at low temperatures, giving a high proportion of ortho-nitro derivatives in good yields.
