Chiral compounds Alicyclics

The cleavage of alicyclic phenyl ketones generally leads to benzene and alicyclic carboxamides. Nevertheless, the use of 1-methyl cyclopropyl phenyl ketone yields benzamide and a cyclopropane. Using this property with a chiral compound, Imposimato and Walborsky (ref. 110) have shown that this reaction proceeds with retention of configuration (Fig. 20). 

Similarly, 6°-metacyclophane forms clathrate complexes with benzene derivatives or alicyclic compounds, where only a little guest selectivity has been found ) The ratio n/m of these crystal lattice (cavity) inclusion compounds varies significantly, e.g., n/m=0.3-0.6 (cyclotricatechylene), 2-6 (tri-O-thymotide). It has been found that tri-O-thymotide resolves optical isomers, e.g., 2-butyl halides, by making host-guest inclusion crystals. These optical resolutions are therefore attributable to the crystal lattice chirality that was induced... 

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