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Generation of new dithia dications from sterically congested 1.9-dithiodibenzothiophenes and their monooxides in concentrated sulfuric acid

โœ Scribed by Naomichi Furukawa; Takeshi Kimura; Yoji Horie; Satoshi Ogawa; Hisashi Fujihara

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
144 KB
Volume
33
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Dithicdibenzothiophenes 2 were prepared by ring contraction of 46dithiothianthrene-S-oxides with n-butyllithium. Both compounds 2 and their monooxides 3 upon dissolution in cont. H2SO4 afforded the corresponding new dithia dications. Electrochemical oxidation of 2 provides the evidence for the neighboring group interaction between the two l,9-sulfenyl sulfur atoms. Sterically congested 1,9-dithiodibenzothiophenes 2 were readily prepared by coupling reactions of the corresponding 4.h-dithiosubstituted thianthrene-S-oxides 1. 1 Since compounds 2a,b have two closely located sulfur atoms of the I,9 positions, they should provide a new dicationic S-S a-bond on oxidation.233 This paper

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I , 9-Dithia substituents in dibenzothiophenes are in close proximity, being within the van der Waals S-S contact distance (3.70 A) [I], and hence, these two sulfur atoms affect each other by strong through-space interaction. Cyclic and acyclic dibenzothiophene derivatives bearing two sulfur atoms a