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New route to 4,4,6,7-tetrasubstituted pentacyclo[6.3.0.02,6.03.10.05,9]undecanes

✍ Scribed by Alexander M. Aleksandrov; Susan A. Bourne; Mariusz Krawiec; Tonis J.Pehk; Alexander E. Petrenko; William H. Watson

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
398 KB
Volume
50
Category
Article
ISSN
0040-4020

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✦ Synopsis

Abstractz The reactions of 3,6-dibromo-2,7-dioxotetracyclo[6.3.0.0 4s".6s9]undecane with organomagnesium halides are investigated as a method of preparing unusual tetrasubstitutcd pentacycloundwanes (D,-trishomocubanes). The tetrasubstituted pentacycloundeames have been characterized and product geometries confirmed by NMR and X-ray crystal structure analysis. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ (11) exhibits a sterically locked phenyl group with a rotation barrier > 17 kcal/mol which should make possible the preparation of stable rotational isomers with o-or m-substituted phenyl groups. INTRODUCI'ION The synthesis of the strained polyfunctionalized pentacycloundecane (PCUD) series of molecules by photochemical methods has been investigated extensively. ' Some derivatives of the PCUD system

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the independent rings which comprise the compound. I.r. and Raman spectra were recorded, and a vibrational analysis was performed on the spectral quantities. The standard thermodynamic properties in the ideal-gas state were calculated in the temperature range 100 K to 1000 K. The calculated standard