Synthesis of Dihalo-Substituted Analogues of Tröger’s Base from ortho- and meta-Substituted Anilines.

Summary, in English

For the first time, ortho- and meta-halo-substituted anilines were successfully condensed with formaldehyde to dihalo-substituted analogues of Trögers base. By using paraformaldehyde and TFA, yields of 2-85% of these potential supramolecular building blocks were obtained. Even the inconceivable achievement of condensing anilines unsubstituted in para-position to analogues of Trögers base was successful. Adding our present results to our previous, makes it now possible to synthesize analogues of Trögers base halo-substituted in almost any desired position in each of its two aromatic rings. In addition the first X-ray structure of a dihalo-substituted analogue of Trögers base, 3,9-dibromo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (17), is presented. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

• Author: Anna Hansson; Jacob Jensen; Ola Wendt; Kenneth Wärnmark
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2003
• Language: English
• Pages: 3179-3188
• Publication/Series: European Journal of Organic Chemistry
• Volume: 2003
• Issue: 16
• Links: http://dx.doi.org/10.1002/ejoc.200300144
• Document type: Journal article
• Publisher: John Wiley & Sons Inc.
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 1434-193X