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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Show full item recordAbstract
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
Projects:
DOI: 10.5935/0103-5053.20130144
ISSN: 0103-5053