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

Hansson, Anna LU ; Jensen, Jacob LU ; Wendt, Ola LU and Wärnmark, Kenneth LU (2003) In European Journal of Organic Chemistry 2003(16). p.3179-3188
Abstract
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,... (More)
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) (Less)
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organization
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Contribution to journal
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published
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in
European Journal of Organic Chemistry
volume
2003
issue
16
pages
3179 - 3188
publisher
John Wiley & Sons
external identifiers
  • wos:000184932600020
  • scopus:0041475910
ISSN
1434-193X
DOI
language
English
LU publication?
yes
id
9846069a-c4b0-485c-83be-bd62e26a6af4 (old id 128563)
date added to LUP
2007-07-09 13:42:18
date last changed
2018-05-29 11:22:05
@article{9846069a-c4b0-485c-83be-bd62e26a6af4,
  abstract     = {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       = {Hansson, Anna and Jensen, Jacob and Wendt, Ola and Wärnmark, Kenneth},
  issn         = {1434-193X},
  language     = {eng},
  number       = {16},
  pages        = {3179--3188},
  publisher    = {John Wiley & Sons},
  series       = {European Journal of Organic Chemistry},
  title        = {Synthesis of Dihalo-Substituted Analogues of Tröger’s Base from ortho- and meta-Substituted Anilines.},
  url          = {http://dx.doi.org/},
  volume       = {2003},
  year         = {2003},
}