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Debromination of endo-(+)-3-Bromocamphor with Primary Amines

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2013
1220.pdf (3.678Mb)
Authors
Marković, Svetlana
Markovic, Violeta
Joksovic, Milan D.
Todorović, Nina
Joksovic, Ljubinka
Divjakovic, Vladimir
Trifunović, Snežana
Article (Published version)
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Abstract
Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.
Keywords:
3-bromocamphor / primary amines / reductive debromination / reaction mechanism / DFT
Source:
Journal of the Brazilian Chemical Society, 2013, 24, 7, 1099-
Publisher:
  • Soc Brasileira Quimica, Sao Paulo
Funding / projects:
  • Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes (RS-172016)

DOI: 10.5935/0103-5053.20130144

ISSN: 0103-5053

WoS: 000322727100003

Scopus: 2-s2.0-84880656725
[ Google Scholar ]
3
3
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1222
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Marković, Svetlana
AU  - Markovic, Violeta
AU  - Joksovic, Milan D.
AU  - Todorović, Nina
AU  - Joksovic, Ljubinka
AU  - Divjakovic, Vladimir
AU  - Trifunović, Snežana
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1222
AB  - Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.
PB  - Soc Brasileira Quimica, Sao Paulo
T2  - Journal of the Brazilian Chemical Society
T1  - Debromination of endo-(+)-3-Bromocamphor with Primary Amines
VL  - 24
IS  - 7
SP  - 1099
DO  - 10.5935/0103-5053.20130144
ER  - 
@article{
author = "Marković, Svetlana and Markovic, Violeta and Joksovic, Milan D. and Todorović, Nina and Joksovic, Ljubinka and Divjakovic, Vladimir and Trifunović, Snežana",
year = "2013",
abstract = "Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.",
publisher = "Soc Brasileira Quimica, Sao Paulo",
journal = "Journal of the Brazilian Chemical Society",
title = "Debromination of endo-(+)-3-Bromocamphor with Primary Amines",
volume = "24",
number = "7",
pages = "1099",
doi = "10.5935/0103-5053.20130144"
}
Marković, S., Markovic, V., Joksovic, M. D., Todorović, N., Joksovic, L., Divjakovic, V.,& Trifunović, S.. (2013). Debromination of endo-(+)-3-Bromocamphor with Primary Amines. in Journal of the Brazilian Chemical Society
Soc Brasileira Quimica, Sao Paulo., 24(7), 1099.
https://doi.org/10.5935/0103-5053.20130144
Marković S, Markovic V, Joksovic MD, Todorović N, Joksovic L, Divjakovic V, Trifunović S. Debromination of endo-(+)-3-Bromocamphor with Primary Amines. in Journal of the Brazilian Chemical Society. 2013;24(7):1099.
doi:10.5935/0103-5053.20130144 .
Marković, Svetlana, Markovic, Violeta, Joksovic, Milan D., Todorović, Nina, Joksovic, Ljubinka, Divjakovic, Vladimir, Trifunović, Snežana, "Debromination of endo-(+)-3-Bromocamphor with Primary Amines" in Journal of the Brazilian Chemical Society, 24, no. 7 (2013):1099,
https://doi.org/10.5935/0103-5053.20130144 . .

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