Tropilidene easily adds six atoms of chlorine forming a complex mixture of stereoisomeric 1,2,3,4,5,6-hexachlorocycloheptanes.
The stereoisomers described can be separated by frontal chromatography on aluminum oxide.
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Liberman, A.L., Pryanishnikova, M.A. & Golovkin, G.V. On the addition of chlorine to tropilidene. Russ Chem Bull 16, 2014–2016 (1967). https://doi.org/10.1007/BF00909608
- Complex Mixture