Diacenaphtho[1,2-c:1,2-e]-1,2-dithiin: synthesis, structure and reactivity |
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Authors: | Richard D Adams Burjor Captain Jack L Smith Jr |
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Institution: | Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter Street, GRSC 109, Columbia, SC 29208, USA |
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Abstract: | Diacenaphtho1,2-c:1′,2′-e]-1,2-dithiin 2 was synthesized in 23% yield by the reaction of acenaphthylene with elemental sulfur at 120 °C. This reaction also afforded either diacenaphtho1,2-b:1′,2′-d]thiophene 1 or diacenaphtho1,2-b:1′,2′-e]-dihydroe]-1,4-dithiin 3 depending on the reaction time. Compound 2 was desulfurized and converted to 1 under UV-vis irradiation in a benzene solution. Reaction of 2 with Pt(COD)2 yielded the complex Pt(COD)(C24H12S2) 4 (COD=1,5-cyclooctadiene) by insertion of a Pt(COD) group into the S-S bond of 2. When heated, 4 was desulfurized and converted to 1 by elimination of a (COD)PtS grouping. Compounds 1-4 were characterized crystallographically. |
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Keywords: | Diacenaphthothiophene Diacenaphthodithiin Diacenaphthodihydrodithiin Platinum insertion |
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