Is there stereoelectronic control in hydrolysis of cyclic guanidinium ions?

To assess stereoelectronic effects in the cleavage of tetrahedral intermediates, a series of five-, six-, and seven-membered cyclic guanidinium salts was synthesized. If stereoelectronic control by antiperiplanar lone pairs is operative, these are expected to hydrolyze with endocyclic C-N cleavage to acyclic ureas. However, hydrolysis in basic media… (More)