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General Protocols for the Synthesis of C(2)-Symmetric and Asymmetric 2,8-Disubstituted Analogues of Tröger's Base via Efficient Bromine-Lithium Exchanges of 2,8-Dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine.

Jensen, Jacob LU ; Tejler, Johan LU and Wärnmark, Kenneth LU (2002) In Journal of Organic Chemistry 67(17). p.6008-6014
Abstract
Methods for facile synthesis of symmetric and unsymmetric functionalized analogues of Tröger's base were developed with use of 2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (2) as the starting material. C(2)-symmetric 2,8-disubstituted analogues of Tröger's base (4a-f) were synthesized via double bromine-lithium exchange of 2 followed by quench with electrophiles. Desymmetrization via single bromine-lithium exchange of 2, followed by quench with electrophiles, afforded asymmetric analogues of Tröger's base (6a-g). Further reaction of 2-bromo-8-(trimethylsilyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (6b) produced 7a-c via single bromine-lithium exchange and subsequent quench with electrophiles.
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
67
issue
17
pages
6008 - 6014
publisher
The American Chemical Society
external identifiers
  • pmid:12182636
  • wos:000177559800023
  • scopus:0037162731
ISSN
1520-6904
DOI
10.1021/jo025823g
language
English
LU publication?
yes
id
18524f07-09e5-42c3-bd7d-40090611c6cb (old id 109984)
date added to LUP
2007-07-10 11:35:22
date last changed
2017-01-01 05:05:16
@article{18524f07-09e5-42c3-bd7d-40090611c6cb,
  abstract     = {Methods for facile synthesis of symmetric and unsymmetric functionalized analogues of Tröger's base were developed with use of 2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (2) as the starting material. C(2)-symmetric 2,8-disubstituted analogues of Tröger's base (4a-f) were synthesized via double bromine-lithium exchange of 2 followed by quench with electrophiles. Desymmetrization via single bromine-lithium exchange of 2, followed by quench with electrophiles, afforded asymmetric analogues of Tröger's base (6a-g). Further reaction of 2-bromo-8-(trimethylsilyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (6b) produced 7a-c via single bromine-lithium exchange and subsequent quench with electrophiles.},
  author       = {Jensen, Jacob and Tejler, Johan and Wärnmark, Kenneth},
  issn         = {1520-6904},
  language     = {eng},
  number       = {17},
  pages        = {6008--6014},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {General Protocols for the Synthesis of C(2)-Symmetric and Asymmetric 2,8-Disubstituted Analogues of Tröger's Base via Efficient Bromine-Lithium Exchanges of 2,8-Dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine.},
  url          = {http://dx.doi.org/10.1021/jo025823g},
  volume       = {67},
  year         = {2002},
}