Mechanism of Nucleophilic Substitution Reactions of o-Nitrobenzenesulfenamides: Evidence for a Substitution Proceeding through a Sulfuranide Intermediate
o-Nitrobenzenesulfenamides (1) undergo acid-catalyzed methanolysis (eq 2) in acetonitrile-methanol, affording methyl o-nitrobenzenesulfenate (2).They also undergo acid-catalyzed reaction with a thiol, giving an alkyl o-nitrophenyl disulfide (eq 3).In MeCN
Kice, John L.,Kutateladze, Andrei G.
p. 3298 - 3303
(2007/10/02)
SYNTHESIS AND REACTIONS OF TRANS-2-(2'-NITROPHENYLTHIO)-1-CHLOROINDANE
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.
Einbaum, Priit,Suschitzky, Hans
p. 231 - 240
(2007/10/02)
PARTICIPATION OF ELECTRONIC ORGANIC COMPOUNDS OF DIVALENT SULFUR IN CATALYTIC CONVERSIONS. II. CATALYTIC EXCHANGE REACTION OF N-MONOSULFENYLATED AMINES WITH S-ESTERS OF THIOCARBOXYLIC ACID
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Parfenov, E. A.,Fomin, V. A.
p. 947 - 953
(2007/10/02)
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