80805-54-5

Upstream product

• 532-27-4 1-chloroacetophenone 
• 100-00-5 4-chlorobenzonitrile 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 98-86-2 acetophenone 
• 5367-28-2 5-chloro-2-nitrotoluene 
• 80805-67-0 (Z)-2-(5-Chloro-2-nitro-phenyl)-3-dimethylamino-1-phenyl-propenone 

Downstream Products

• 80805-59-0 2-(5-Chloro-2-nitro-phenyl)-1-phenyl-ethanone oxime 
• 80806-03-7 4-Chloro-2-(2-methylamino-2-phenyl-ethyl)-phenylamine 
• 80805-85-2 N-[2-(5-Chloro-2-nitro-phenyl)-1-phenyl-ethyl]-formamide 
• 80805-62-5 C₁₆H₁₃ClN₂O₄ 
• 81170-81-2 7-chloro-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine 
• 791015-39-9 2-(5-Chloro-2-nitro-phenyl)-1-phenyl-ethylamine 
• 766461-33-0 [2-(5-Chloro-2-nitro-phenyl)-1-phenyl-ethyl]-methyl-amine 
• 81170-82-3 7-chloro-4,5-dihydro-2-ethyl-3-methyl-4-phenyl-3H-1,3-benzodiazepine 

Relevant academic research and scientific papers

VICARIOUS NUCLEOPHILIC SUBSTITUTION OF HYDROGEN IN NITROARENES WITH α-CHLORO-ENOLATE ANIONS

Reactions of α-chloroketones with nitroaromatic compounds are described.They follow Vicarious Nucleophilic Substitution of Hydrogen pattern leading to nitroarylated ketones in moderate to good yields.

Nucleophilic Addition of Silyl Enol Ethers to Aromatic Nitro Compounds: Scope and Mechanism of Reaction

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 SUBSTITUTION OF 4-CHLOROQUINOLINE 1-OXIDE AND RELATED COMPOUNDS BY MEANS OF HYDRIDE ELIMINATION

The reaction of 4-chloroquinoline 1-oxide (1) with pinacolone and t-BuOK in t-BuNH2 at -10 ca. -15 deg C gives 4-chloro-2-pinacolylquinoline 1-oxide in good yield by means of hydride-elimination.Similar reactions of 1 with acetone, 2-butanone, acetophenone, and ethyl and t-butyl acetates occur when treated with t-BuOK or n-BuLi in t-BuNH2 at -10 ca. -15 deg C, or t-BuOK, KNH2 or NaNH2 in liq NH3 at -70 deg C.Reactions of this type proceed also with quinoline 1-oxide (2), 3-bromoquinoline 1-oxide (3), p-chloronitrobenzene (4) and nitrobenzene.