The synthesis and spectra of some heterocyclic fulvalenes

✍ Scribed by G.J. Heeres; H. Wynberg

• Publisher: Elsevier Science
• Year: 1972
• Tongue: French
• Weight: 673 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)88942-0

✦ Synopsis

W-The heterofulvalenes X-XIV, XXIII and XXVI have been synthesized. The effect of overcrowding on their spectral properties is discussed. The last step in the synthetic schemes is a dehydration reaction of the appropriate carbinols. The great difference in reactivity of these intermediate carbinols in the dehydration reactions is striking.

The dehydration of the fluorenylhydroxycyclopentadithiophenes could be achieved in acetic acid with 1-3 drops concentrated hydrochloric acid. All other dehydration methods like oxalylchloride, Pz05, thionylchloride in pyridine, ptoluenesulfonic acid in benzene, HBr gas in acetic acid, PBr, in benzene and BF3 in ether failed to yield fulvalenes.