35143-08-9Relevant articles and documents
Visible-Light-Promoted Remote C-H Functionalization of o-Diazoniaphenyl Alkyl Sulfones
Du, Shaofu,Kimball, Elizabeth Ann,Ragains, Justin R.
supporting information, p. 5553 - 5556 (2017/10/25)
Visible-light irradiation of ortho-diazoniaphenyl alkyl sulfones in the presence of Ru(bpy)32+ results in remote Csp3-H functionalization. Key mechanistic steps in these processes involve intramolecular hydrogen atom transfer from Csp3-H bonds to aryl radicals to generate alkyl/benzyl radicals. Subsequent polar crossover occurs by single-electron oxidation of the alkyl/benzyl radicals to carbenium ions that then intercept nucleophiles. We have developed remote hydroxylations, etherifications, an amidation, and C-C bond formation processes using this strategy.
The different electronic natures displayed by the alkylthio groups in simple and higher conjugated aniline systems
Han, Chien-Chung,Balakumar,Thirumalai,Chung, Ming-Tsu
, p. 3511 - 3516 (2008/09/17)
Systematic studies based on 1H NMR and 13C NMR indicated that the alkylthio group behaves as a weak electron-withdrawing group in a simple aniline system like 2-butylthioaniline, while the same alkylthio group clearly acted as a resonance electron-donating group in higher conjugated aniline trimer systems, like butylthio-substituted PDA (mono-PDA) and dibutylthio-substituted PDA (2,6-diPDA). The formation of 2,6-diPDA as the major byproduct during the preparation of mono-PDA from PDI and butane-1-thiol provided additional support for the resonance electron donating nature of the butylthio group in these aniline trimer systems. Furthermore, CV studies also clearly indicated that the redox potential E° (vs. SCE) of the aniline trimer systems decreased with the increase in the number of butylthio groups, further confirming the electron-donating nature of the butylthio group in these higher conjugated trimer systems. The Royal Society of Chemistry 2006.
KF-alumina immobilized in ionic liquids: A novel heterogeneous base for heterocyclization of alkylsulfanylphenylamines into 1,4-benzothiazine
Chhikara, Bhupender S.,Mishra, Anil K.,Tandon, Vibha
, p. 1057 - 1065 (2007/10/03)
A rapid and convenient synthetic methodology for the cyclocondensative transformation of various alkylsulfanylphenylamines with bromoacetyl bromide by supporting on KF-alumina in ionic liquids [bmim] [Br] and [bmim][BF 4] has been developed to obtain 3-oxo-1,4-benzothiazine in good yields. The product is easily obtained by extraction with ethyl acetate and concentrating under vacuum. Easy recovery of ionic liquid and use in consecutive reactions is also reported.