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A new method for the preparation of hexachlorofulvene has been developed. The aluminum chloride catalyzed reaction of carbon tetrachloride and 1,2,3,4,5-pentachlorocyclopentadiene gave 4, which underwent facile dechlorination to the desired 1. The behavior of 1 under Diels-Alder conditions was investigated. Reaction with cyclopentadiene showed that 1 acts primarily as the dienophile to form 5. Isomer 7 was also formed and indicated that 1 may also react as a diene. Hexachlorofulvene is an electron-deficient diene, but less reactive than hexachlorocyclopentadiene, possibly reflecting some stabilization from the dipolar resonance form. Treatment of 1 with A1C13 gave a dimer and a difulvene.

Aus dem Pentachlorcyclopentadien (I) erhält man mit Tetrachlorkohlenstoff in Gegenwart von Aluminiumchlorid das Substitutionsprodukt (II), das, z.B. mit Triäthylphosphit, zum Hexachlorfulven (III) dechloriert wird.