The 1,4-dithiin ring opening in isothioquinanthrene

Article abstract of DOI:10.1080/10426509608046349

The 1,4-dithiin ring opening reactions in isothioquinanthrene 1 (1,4-dithiino[2,3-c;6,5-c']diquinoline) with selected S-, O and Se-nucleophiles in DMSO or DMF at 20-70°C proceeded with cleavage of only one C_4-quinolinyl - S bond to give alkali metal salts of 4-substiluted 4′-mercapto-3,3′-diquinolinyl Sulfides 2a-2h and 6 as primary products and after S-alkylation in aqueous sodium hydroxide solution 4-substituted 4′-alkylthio-3,3′-diquinolinyl Sulfides 3-5 and 7 as the final products. In contrast to sulfides 2a-2h sulfide 3a reacted with S-nucleophiles (sodium alkanethiolates) with cleavage of the C_3-quinolinyl - S, C_4-quinolinyl - S and CH₃ - S bonds to form 3,4-dialkylthioquinolines 8a-8e as the main compounds. In the case of relatively bulky S-nucleopbiles (the 2-methyl-2-propanethiolate and to some extent the ethanethiolate anions) the cleavage of the C_3-quinolinyl - S by a vicarious nucleophile (the methanethiolate anion, liberated in the cleavage of the C_4-quinolinyl - S bond) was observed.

Full text of DOI:10.1080/10426509608046349

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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THE 1,4-DITHIIN RING OPENING IN
ISOTHIOQUINANTHRENE
Krystian Pluta a
a Department of Organic Chemistry , Silesian School of Medicine ,
Jagielloríska Str. 4, 41-200, Sosnowiec, Poland
Published online: 04 Oct 2006.
To cite this article: Krystian Pluta (1996) THE 1,4-DITHIIN RING OPENING IN ISOTHIOQUINANTHRENE,
Phosphorus, Sulfur, and Silicon and the Related Elements, 112:1-4, 57-69, DOI:
10.1080/10426509608046349
To link to this article: http://dx.doi.org/10.1080/10426509608046349
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