1009-36-5Relevant articles and documents
Charge control in the S(N)Ar reaction. Meta substitution with respect to the activating nitro group in 3,4-dihalogenonitrobenzenes
Cervera,Marquet,Martin
, p. 2557 - 2564 (1996)
The reactions of 3-fluoro-4-chloronitrobenzene and of 3,5-difluoro-4-chloronitrobenzene with thiophenoxide anion lead to predominant substitution of the chlorine atom through S(N)Ar orbital-controlled processes. However, when harder nucleophiles (methoxide anion) are used, the substitution of a fluorine atom meta with respect to the activating nitro group becomes apparent in the reaction of 3-fluoro-4-chloronitrobenzene, predominant in the reaction of 5-fluoro-4-chloro-3-methyoxynitrobenzene, and almost exclusive in the reaction of 3,5-difluoro-4-chloronitrobenzene. Kinetic measurements and theoretical calculations indicate that the observed meta substitution of a fluorine atom is a S(N)Ar charge-controlled reaction with a loosely bonded transition state.
Halogenation and DNA cleavage via thermally stable arenediazonium camphorsulfonate salts
Vajpayee, Vaishali,Moon, Mi Eun,Lee, Sunmi,Ravikumar, Sambandam,Kim, Hyunuk,Ahn, Byungchan,Choi, Seoyoon,Hong, Soon Ho,Chi, Ki-Whan
, p. 3511 - 3517 (2013/04/23)
A series of stable arenediazonium camphorsulfonate salts (2a-2j) were synthesized by simple diazotization of several aromatic amines in the presence of sodium nitrite and camphorsulfonic acid. All the new arenediazonium camphorsulfonates, which were characterized by multinuclear (1H and 13C) NMR, IR, DSC, and X-ray diffraction analysis (2e and 2f) provide unambiguous proof for the molecular structures of 2e and 2f. The efficient application of these salts in halogenation reactions was studied in solvent and solvent-free conditions and the DNA cleavage activity was also assessed. These arenediazonium camphorsulfonate salts are noticed as efficient DNA cleaving agents.
Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts
Lee, Young Min,Moon, Mi Eun,Vajpayee, Vaishali,Filimonov, Victor D.,Chi, Ki-Whan
experimental part, p. 7418 - 7422 (2010/10/01)
Arenediazonium tosylate salts have been successfully employed as a new and efficient reagent in halogenation reactions. A novel and economic protocol has been developed for the bromination and chlorination of various anilines using arenediazonium tosylate salts. A wide variety of reaction conditions were studied in acetonitrile at either room temperature or 60 °C in the presence or absence of catalyst with good to excellent yields. A surprising result showed the formation of acetanilides as a major product of aniline and methyl-substituted aniline halogenations in high yields.
Compounds for the modulation of PPARgamma activity
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, (2008/06/13)
Modulators of PPARγ activity are provided which are useful in pharmaceutical compositions and methods for the treatment of conditions such as type II diabetes and obesity.