engleski

Rigid Alicyclic Molecules from Bicyclo[2.2.1]hept-2-enes (=8, 9, 10-Trinorbornenes) and 1, 4-Dipyridin-2-ylphthalazines as Stereoselective Coupling Agents

The 1, 4-bis(2-pyridyl)-2, 3-phthalazines were used for the preparation of rigid polycyclic molecules from bicyclo[2.2.1] alkenes. Cycloaddition reactions with norbornenes give coupled products in a stereoselective manner. In these reactions phthalazines deliver new bicyclo[2.2.2] moiety at a junction of two norbornene units, which could bear appropriate functional groups. The crystal structure of a key cycloadduct was also determined. In continuation, relative reactivities for a series of phthalazines were estimated by DFT calculations at B3LYP/6-31G* level. Calculations indicate an increase of reactivity by diminishing aromaticity of phthalazine moiety. Finally, experimentally observed stereoselectivities of the phthalazine reactions with norbornenes are readily predicted by DFT calculations.

cycloadditions ; high pressure ; norbornenes ; DFT calculations ; X-ray analysis

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