97522-01-5Relevant academic research and scientific papers
Process of preparing nitrodihydroaryl carbonyl compounds
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, (2008/06/13)
Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.
Nucleophilic Addition of Silyl Enol Ethers to Aromatic Nitro Compounds: Scope and Mechanism of Reaction
RajanBabu, T. V.,Reddy, G. S.,Fukunaga, Tadamichi
, p. 5473 - 5483 (2007/10/02)
In sharp contrast to alkali-metal enolates, silyl enol ethers and ketene silyl acetals add to aromatic nitro compounds in the presence of a fluoride ion source to give the intermediate dihydroaromatic nitronates, which can be observed by NMR.In situ oxidation of the intermediate with bromine or DDQ yields α-nitroaryl carbonyl compounds in moderate-to-high yields.The reaction is applicable to alkyl-, alkoxy-, and halogen-substituted nitrobenzenes as well as to heterocyclic and condensed nitroaromatic compounds.While substitution ortho to the nitro group predominates with sterically undemanding silyl reagents, para-substitution products are exclusively obtained with bulky reagents.However, by blocking the para position with an appropriate group such as chlorine, the addition can be directed to the ortho position.Halogen atoms of halogenated nitroaromatics and p-nitrocumenyl chloride are not displaced in the reaction, suggesting the absence of radical ion intermediates.Dihydroaromatic nitro derivatives ca be isolated in some cases, such as anthracene and naphthalene systems which are less prone to rearomatize.
Nucleophilic Addition of Silyl Enol Ethers to Aromatic Nitro Compounds: A Facile Synthesis of α-Nitroaryl Carbonyl Compounds
RajanBabu, T. V.,Fukunaga, Tadamichi
, p. 4571 - 4572 (2007/10/02)
Silyl enol ethers and silyl ketene acetals add to aromatic nitro compounds in the presence of fluoride ion sources (e.g. tris(dimethylamino)sulfonium difluorotrimethylsiliconate (TASF)) to give, after oxidation, α-nitroaryl carbonyl compounds.
