100461-60-7Relevant articles and documents
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.