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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
publishing date
type
Contribution to journal
publication status
published
subject
in
European Journal of Organic Chemistry
volume
2003
issue
16
pages
3179 - 3188
publisher
John Wiley & Sons Inc.
external identifiers
  • wos:000184932600020
  • scopus:0041475910
ISSN
1434-193X
DOI
10.1002/ejoc.200300144
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Inorganic chemistry (ceased) (LUR000010)
id
9846069a-c4b0-485c-83be-bd62e26a6af4 (old id 128563)
date added to LUP
2016-04-01 12:14:19
date last changed
2022-02-18 19:49:44
@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 Inc.}},
  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/10.1002/ejoc.200300144}},
  doi          = {{10.1002/ejoc.200300144}},
  volume       = {{2003}},
  year         = {{2003}},
}