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RESEARCH PRODUCT
An Efficient Synthesis of Rubin’s Aldehyde and its Precursor 1,3,5-Tribromo-2,4,6-tris(dichloromethyl)benzene
Herbert MeierChristoph HolstDieter Schollmeyersubject
Trischemistry.chemical_classificationChemistryGeneral ChemistryPhotochemistryMedicinal chemistryAldehydechemistry.chemical_compoundsymbols.namesakeIntramolecular forcesymbolsPetroleum etherVan der Waals radiusBenzenedescription
2,4,6-Tribromobenzene-1,3,5-tricarboxaldehyde (4) can be efficiently prepared in two reaction steps from 1,3,5-tribromobenzene. The intermediate 1,3,5-tribromo-2,4,6-tris(dichloromethyl)benzene (3) crystallizes from petroleum ether in its C3h structure. However, in CDCl3 solution it exists at room temperature in two isomeric forms: 3a (C3h) and 3b (Cs) (1:1.15).The intramolecular Br・・・Cldistances are much smaller than the sum of the van der Waals radii. Therefore, the exocyclic C-C bonds show a hindered rotation.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-09-01 | Zeitschrift für Naturforschung B |