Diacenaphtho[1,2-c: 1′,2′-e]-1,2-dithiin: Synthesis, structure and reactivity

Richard D. Adams, Burjor Captain, Jack L. Smith

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Diacenaphtho[1,2-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 diacenaphtho[1,2-b:1,2-d]thiophene 1 or diacenaphtho[1,2-b:1,2-e]- dihydro[e]-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.

Original languageEnglish
Pages (from-to)65-70
Number of pages6
JournalJournal of Organometallic Chemistry
Volume689
Issue number1
DOIs
StatePublished - Jan 5 2004
Externally publishedYes

Fingerprint

Thiophenes
crack opening displacement
Thiophene
Benzene
Sulfur
reactivity
Irradiation
synthesis
thiophenes
reaction time
insertion
elimination
sulfur
benzene
acenaphthylene
1,5-cyclooctadiene
irradiation

Keywords

  • Diacenaphthodihydrodithiin
  • Diacenaphthodithiin
  • Diacenaphthothiophene
  • Platinum insertion

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Diacenaphtho[1,2-c : 1′,2′-e]-1,2-dithiin: Synthesis, structure and reactivity. / Adams, Richard D.; Captain, Burjor; Smith, Jack L.

In: Journal of Organometallic Chemistry, Vol. 689, No. 1, 05.01.2004, p. 65-70.

Research output: Contribution to journalArticle

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