Open AccessThe improved synthesis, Diels‐Alder reactions, and desulfuration of trithio‐1,8‐naphthalic anhydride
Author(s) -
Huang TianBao,
Qian Xuhong,
Tao ZhiFu,
Wang Ke,
Song GongHua,
Liu LingFei
Publication year - 1999
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/(sici)1098-1071(1999)10:2<141::aid-hc7>3.0.co;2-b
Subject(s) - chemistry , heteroatom , lewis acids and bases , organic chemistry , microanalysis , diels–alder reaction , nuclear magnetic resonance spectroscopy , ring (chemistry) , catalysis
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‐1,8‐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. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 141–146, 1999