Keywords:Cross-coupling / Cycloadditions / Liquid crystals / Small ring systems / Structure elucidation Additions of ethyl or tert-butyl diazoacetates to 4-substituted cyclopentenes 6 and 17 under dirhodium tetraacetate/tetraoctanoate catalysis led to mixtures of tert-butyl endo, exoand exo,exo-3-carboxyl(aryl)bicyclo[3.1.0]hexane-6-carboxylates 7 and 18 in yields of 54−90% from which exo,exodiastereomers were isolated in yields of 39−63%. Diester exo,exo-7 was saponified and converted into diaryl diesters exo,exo-9a,b in overall yields of 42 and 46%, respectively. The esters exo,exo-18 were reduced to the corresponding hydroxymethyl derivatives, these were transformed to the iodomethyl compounds which in turn were coupled with various alkylmagnesium halides, via Li 2 CuCl 4 catalysis, to give 3-aryl-6-alkylbicyclo[3.1.0]hexyl derivatives exo,exo-21 in overall yields of 72−83%. Fluorinated 3-(2-arylethyl)-6-pentylbicyclo[3.1.0]hexane exo,exo-32 could be prepared in five steps from 4-ethoxy-2,3-difluorobenzaldehyde 26a ad-

Cyclopentane derivativesCyclopentane derivatives Q 0030 Cyclopropyl Building Blocks in Organic Synthesis. Part 96. Novel Liquid Crystalline Compounds Containing Bicyclo[3.1.0]hexane Core Units. -Compared to isomorphous liquid crystalline compounds containing a 1,4-disubstituted cyclohexane moiety, the newly prepared bicyclic compounds (I) have comparable dielectric and anisotropic anisotropies, but, as a rule, the bicyclo[3.1.0]hexane moiety decreases the transition temperature. In general, the bicyclo[3.1.0]hexane derivatives have a poorer mesogenic potential than the isomorphous cyclohexane derivatives. -(KOZHUSHKOV, S. I.; LANGER, R.; YUFIT, D. S.; HOWARD, J. A. K.; SCHILL, H.; DEMUS, D.; MIYAZAWA, K.; DE MEIJERE*, A.; Eur.

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