The improved synthesis, diels-alder reactions, and desulfuration of trithio-1,8-naphthalic anhydride

  • Tian Bao Huang*
  • , Xuhong Qian
  • , Zhi Fu Tao
  • , Ke Wang
  • , Gong Hua Song
  • , Ling Fei Liu
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

In the presence of a strong Lewis base, such as Et3N, trithio-1,8-naphthalic anhydride (3) is easily oxidized. Two improved syntheses of trithio-1,8-naphthalic anhydride (3) are described. Trithio-1,8-naphthalic anhydride (3) undergoes Diels-Alder reactions with electron-deficient alkenes to give novel fused heterocyclic compounds (6-11) that then can undergo a novel, gradual desulfuration dimerization with triethyl phosphite to afford 12 and its analogs 13 and 14. The structures of 6-14 are confirmed by microanalysis, IR, and NMR spectroscopy, and MS.

Original languageEnglish
Pages (from-to)141-146
Number of pages6
JournalHeteroatom Chemistry
Volume10
Issue number2
DOIs
StatePublished - 1999
Externally publishedYes

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