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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
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
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1222
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