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Experimental evidence in support of transannular interactions in diketones

The acid catalyzed condensation of polycyclic ketones 1-4 with thiadithiols was carried out. The reaction of ketone 1 with thiadithiols 5 and 6 afforded corresponding crown ethers 7 and 8 respectively. However all diketones 2-4 reacted with 5 or 6 to give corresponding ethylene dithioketals 9-13. To the best of our knowledge, these results provide the first example of chemical evidence for the operation of transannular interactions in rigid polycarbocyclic systems.

diketones ; transannular interactions ; thiadithiols ; dithioketals

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