Debromination of endo-(+)-3-Bromocamphor with Primary Amines
Joksovic, Milan D.
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 / DFT
Source:Journal of the Brazilian Chemical Society, 2013, 24, 7, 1099-
- Soc Brasileira Quimica, Sao Paulo