Electrophilic substitution of the acinitro group by an arylthio group in the dianion of 1,4-dinitrocyclooctatetraene

descriptionPublicationkeyboard_double_arrow_right Article 01 Nov 1986 English Publisher:Springer Science and Business Media LLCJournal:Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, volume 35, pages 2,375-2,378 (issn: 0568-5230, eissn: 1573-9171,

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Authors: Z. V. Todres; G. Ts. Ovsepyan;

doi: 10.1007/bf00953361

Electrophilic substitution of the acinitro group by an arylthio group in the dianion of 1,4-dinitrocyclooctatetraene

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Abstract

The dianion of 1,4-dinitrocyclooctatetraene reacts with 2-nitrobenzenesulfenyl chloride by two parallel pathways: a) substitution of one of the acinitro groups by an arylthio group to form l-nitro-4-(2-nitrophenylthio)cyclooctatetraene and b) a two-electron oxidationreduction with the formation of 2,2'-dinitrodiphenyl disulfide. 4-Nitrobenzenesulfenyl chloride reacts with this dianion to give l-nitro-4-(4'-nitrophenylthio)cyclooctatetraene only upon activation with GaCl3· 2,4-Dinitrobenzenesulfenyl chloride in the presence of GaCl3 reacts with this dianion only by the oxidation-reduction pathway.

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Russian Academy of Sciences
Russian Federation

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