An Efficient Synthesis of Rubin's Aldehyde and its Precursor 1,3,5-Tribromo-2,4,6-tris(dichloromethyl)benzene

作者：Holst Christoph; Schollmeyer Dieter; Meier Herbert^*

来源：Zeitschrift fur Naturforschung Section B-A Journal of Chemical Sciences, 2011, 66(9): 935-938.

DOI：10.5560/ZNB.2011.66b0935

• Polyfunctional Aromatics
• Hexasubstituted Benzenes
• Hindered Rotation

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 C-3h structure. However, in CDCl3 solution it exists at room temperature in two isomeric forms: 3a (C-3h) and 3b (C-s) (1: 1.15). The intramolecular Br center dot center dot center dot Cl distances are much smaller than the sum of the van der Waals radii. Therefore, the exocyclic C-C bonds show a hindered rotation.

• 出版日期2011-9