640-54-0Relevant academic research and scientific papers
Deamination Reactions, 40. Decomposition of 3,3-, 5,5-, and 7,7-Dimethyl-2-norbornanediazonium Ions
Kirmse, Wolfgang,Brandt, Sigrid
, p. 2510 - 2523 (2007/10/02)
gem.-Dimethylnorbornyl cations (3, 5) were generated by decomposition of optically active diazonium ion precursors. 6,1- and 6,2-H shifts were detected by structural isomerization and racemization, respectively.Product distributions and optical activities were profoundly affected by the polarity of the solvent.In weakly polar solvents, substitution reactions were associated with much less racemization than hydrogen shifts.Our observations are incompatible with equilibrating open ions but are reasonably explained in terms of unsymmetrical ion pairs.
