52910-32-4Relevant academic research and scientific papers
Nucleophilic Substitution at Tricyclo1,6>undec-3-ene-11-diazonium Ions
Engbert, Theodor,Kirmse, Wolfgang
, p. 1689 - 1698 (2007/10/02)
The nitrous acid deamination of tricyclo1,6>undec-3-en-11-ylamines 14 and 16 in the presence of sodium bromide afforded the tricyclic bromides 18 and 19 with > 99percent retention.Configurations were assigned by chemical correlation via the carboxylic acids 13 and 15.Deuterium incorporation in D2O indicated some epimerization of the diazonium ions at higher concentrations of sodium bromide, leading to a decrease in stereospecificity.The retention of configuration observed in this study is attributed to the intervention of partially opened cyclopropyl cations.
