267658-48-0Relevant academic research and scientific papers
Synthesis, enantiomer separation, and absolute configuration of 2,6-oxygenated 9-azabicyclo[3.3.1]nonanes
Bieliunas, Vidmantas,Ra?kauskaite, Dovile,Orentas, Edvinas,Ston?ius, Sigitas
, p. 5339 - 5348 (2013/07/26)
The synthesis of the enantiomerically pure N-Boc 9-azabicyclo[3.3.1]nonane- 2,6-dione (4b), a potentially useful chiral building block, from N-Bn and N-Boc 9-azabicyclo[3.3.1]nonane-2,6-diols 2a and 2b was accomplished. The enantiomer resolution of diols
Thia-, Aza-, and selena[3.3.1]bicyclononane dichlorides: Rates vs internal nucleophile in anchimeric assistance
Accurso, Adrian A.,Cho, So-Hye,Amin, Asmarah,Potapov, Vladimir A.,Amosova, Svetlana V.,Finn
supporting information; experimental part, p. 4392 - 4395 (2011/07/30)
Sulfur-, selenium-, and nitrogen-containing compounds bearing leaving groups in the β-position undergo facile substitution chemistry enabled by anchimeric assistance. Here we provide direct comparisons between such systems in the rigid bicyclo[3.3.1]nonane framework easily derived from 1,5-cyclooctadiene. For a series of dichloride electrophiles of this type, the relative reactivities were found to be Se ? (alkyl)N > S ≥ (propargyl)N > (phenyl)N, with the reaction rates at the two extremes differing by more than 3 orders of magnitude. For the N-alkyl case, substitution rates were largely independent of the trapping nucleophile but were strongly dependent on solvent, showing that the process is controlled by the formation of the high-energy three-membered cationic intermediate.
