The improved synthesis, Diels-Alder reactions, and desulfuration of trithio-1,8-naphthalic anhydride

✍ Scribed by Tian-Bao Huang; Xuhong Qian; Zhi-Fu Tao; Ke Wang; Gong-Hua Song; Ling-Fei Liu

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 174 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1999)10:2<141::aid-hc7>3.0.co;2-b

✦ Synopsis

In the presence of a strong Lewis base, such as Et 3 N, trithio-1,8-naphthalic anhydride ( 3) is easily oxidized. Two improved syntheses of trithio-1,8naphthalic 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)(7)(8)(9)(10)(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.