16888-88-3Relevant academic research and scientific papers
SYNTHESIS AND REACTIONS OF TRANS-2-(2'-NITROPHENYLTHIO)-1-CHLOROINDANE
Einbaum, Priit,Suschitzky, Hans
, p. 231 - 240 (2007/10/02)
The title compound was prepared by addition of 2-nitrobenzenesulphenyl chloride to indene, and proton nmr was used to prove its trans-structure.The chloro-substituent could be replaced by ethanol under very mild conditions with retention of configuration owing to anchimeric assistance by the bridging S-atom.Analogous reactions were observed with water and other alcohols (MeOH, Me2CHOH, Me3COH, PhSH).Basic nucleophiles caused dehydro-chlorination to the corresponding indenes.Reduction of the nitro-group resulted in intramolecular cyclisation to give a dihydrobenzindenothiazine 9.Thermolysis of the 2-(2'-nitrophenylthio)-1-azidoindane occurred with ring expansion to give 3-(2'-nitrophenylthio)quinoline.Oxidation of the title compound with m-chloroperoxybenzoic acid produced the corresponding sulphone which smoothly underwent reductive cyclisation to a benzindenothiazinesulphone 20.
STUDIES ON SULFENAMIDES. IX. ANODIC OXIDATION OF N-(o-NITROPHENYLTHIO)ALICYCLIC AMINES
Sayo, Hiroteru,Michida, Takashi
, p. 2541 - 2544 (2007/10/02)
Cation radicals generated by anodic oxidation of N-(o-nitrophenylthio)alicyclic amines (morpholine (1), thiomorpholine(tetrahydro-4H-1,4-thiazine) (2), piperidine (3), pyrrolidine (4)) in acetonitrile were studied by cyclic voltammetry (CV) and electron spin resonance spectroscopy (ESR). 2-(o-Nitrophenylthio)indan-1-ol (6) was obtained from the solution after controlled potential electrolysis (CPE) of 1-3 in acetonitrile containing indene (5) and 0.1 M NaClO4 at a glassy carbon anode.The cation radicals produced by CPE of 1-3 attacked 5 to give 6 as a final product.Keywords-anodic oxidation; 2-nitrobenzenesulfenamide; cyclic voltammetry; electron spin resonance; cation radical; indanol 2-substituted; electrophilic substitution
