Trukhin Alexey, Kruchkov Fedor, Hansen Lars Kr, Kallenborn Roland, Kiprianova Anastasia, Nikiforov Vladimir
Department of Chemistry, St. Petersburg State University, Universitetsky pr. 26, 198504 St. Petersburg, Russia.
Chemosphere. 2007 Apr;67(9):1695-700. doi: 10.1016/j.chemosphere.2006.05.082. Epub 2007 Jan 10.
The primary goal for the study presented here was the preparation and characterisation of enantiomeric pure chlorobornane standards (Toxaphene). In this context, we partially modeled the procedure for Polychloropinene production in the former USSR. The initial reaction was ionic addition of hydrogen chloride to (1S)-alpha-pinene resulting predominantly in (1S)-2-endo-chlorobornane. Further photochlorination gave mixtures of chlorinated terpenes with different average content of Cl per molecule. The resulting mixtures were separated on a silica-gel column and a number of known hepta to decachlorobornanes were identified in fractions with the help of NMR and GC (using electron capture and mass spectrometric detection)--but in very unusual ratios as compared to the technical Toxaphene mixture formerly produced by Hercules (USA). Also several previously unknown congeners were isolated or detected. Three of the isolated congeners were obtained in crystalline state and X-ray crystallography showed their enantiomeric purity.
