Synthesis and Properties of a Bis(2-buteno)-Bridged Bis(adamantane): X-ray and Molecular Dynamic Studies of the trans, trans Isomer

✍ Scribed by Kata Mlinarić-Majerski; Dražen Pavlović; Vjekoslav Milinković; Biserka Kojić-Prodić

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 332 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199806)1998:6<1231::aid-ejoc1231>3.0.co;2-1

✦ Synopsis

The synthesis of the trans,trans isomer of the bis(2-buteno)-3a, 3b and 3c were found. The conformations 3a and 3c have anti-oriented adamantane units, while in 3b the adamantane bridged bis(adamantane) 3 has been developed, and its structure was established by spectral and X-ray structure molecules occupy the syn conformation. By analysing the conformational processes in macrocyclic diene 3, it was analysis. Since the results of dynamic NMR studies indicate that 3 is conformationally mobile and the transition-state free found that the calculated conformation 3a with molecular symmetry of C 2h is very close to that found in solution at -50 energy (∆G c ϶ ) required to interconvert two equivalent conformers was estimated to be ca. 60 kJ mol -1 , the lowest °C, but differs from that which was observed in the solid state by X-ray-crystallographic analysis. energy conformer was subjected to a molecular dynamic simulation at 323 K in the gas phase. Three conformations