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.
(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.
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https://lup.lub.lu.se/record/109984
- author
- Jensen, Jacob LU ; Tejler, Johan LU and Wärnmark, Kenneth LU
- organization
- publishing date
- 2002
- 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 (ACS)
- external identifiers
-
- pmid:12182636
- wos:000177559800023
- scopus:0037162731
- ISSN
- 1520-6904
- DOI
- 10.1021/jo025823g
- 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)
- id
- 18524f07-09e5-42c3-bd7d-40090611c6cb (old id 109984)
- date added to LUP
- 2016-04-01 12:22:26
- date last changed
- 2022-01-27 02:54:09
@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 (ACS)}}, 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}}, doi = {{10.1021/jo025823g}}, volume = {{67}}, year = {{2002}}, }