Tröger's base

(±) -2,8 -dimethyl- 6H, 12H -5 ,11- methanodibenzo [b, f] [ 1,5] diazocine

• 529-81-7 (racemate )
• 21451-74-1 [( 5R, 11R ) - ( )-form ]

Fixed

133-136 ° C

Attention

56.2 mg · kg -1 ( LD50, mouse, i.v.)

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The Tröger base is a after its discoverer, the chemist Julius Tröger (1862-1942), called heterocyclic compound, which is attributed to organic chemistry. Tröger the base includes two pyramidal nitrogen atoms constituting stereocenters. In general, the inversion of pyramidal nitrogen atoms with three different groups ( and a lone pair of electrons ) is very rapid, so that racemize such substances quickly - not so the Tröger base. In the Tröger base both nitrogen atoms are in a bridgehead position, a pyramidal inversion is thus impossible. Therefore, it is of the Tröger base two stable enantiomers which can be separated by chromatography, for example on a chiral stationary phase.

Production

The Tröger base was first synthesized in 1887 starting from p -toluidine and formaldehyde in acid solution. Only in 1935 the correct structural formula was determined. Tröger the base can also be prepared from p- toluidine, dimethyl sulfoxide ( DMSO), and hydrochloric acid or p- toluidine, and hexamethylenetetramine ( HMTA ). All these synthesis methods lead to the racemate of the Tröger base.