Naslov
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

Autori
Margetić, Davor ; Murata, Yasujiro ; Komatsu, Koichi ; Marinić, Željko

Izvornik
Helvetica chimica acta (0018-019X) 92 (2009), 2; 298-312

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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