1,5-diazacyclooctane-3,7-derivatives as precursors of the 3,7-diaza[3.3.0]bicyclooctane and 3,7,10-heterocyclic[3.3.3]propellane ring systems☆

Abstract A simple synthesis of 3,7-disubstituted-1,5-diazacyclooctanes from p-toluenesulfonamides and 3-chloro-2-chloromethylpropene has been developed. Unusual transannular reactions in these eightmembered ring intermediates provide easy access to novel 3,7-diaza[3.3.0]bicyclooctane and 3,7,10-heterocyclic[3.3.3]propellane ring systems.