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

2013
Authors
Marković, SvetlanaMarkovic, Violeta

Joksovic, Milan D.
Todorović, Nina

Joksovic, Ljubinka
Divjakovic, Vladimir
Trifunović, Snežana

Article (Published version)
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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 / DFTSource:
Journal of the Brazilian Chemical Society, 2013, 24, 7, 1099-Publisher:
- Soc Brasileira Quimica, Sao Paulo
Funding / projects:
DOI: 10.5935/0103-5053.20130144
ISSN: 0103-5053
WoS: 000322727100003
Scopus: 2-s2.0-84880656725
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IHTMTY - 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 . .