CHEMISTRY OF AZIDOTROPONES .2. 3-AZIDOTROPONES AND 4-AZIDOTROPONES AND RELATED COMPOUNDS

When treated with oxalyl chloride, the sodium salts of 3- and 4-hydroxytropones afford intermediates of uncertain structure, possibly derivatives of ditropyl ether, which are nevertheless converted into the corresponding chlorotropones on hydrolysis. The behaviour of these compounds in some nucleophilic substitution reactions is qualitatively examined; displacement of halogen by azide ion occurs normally, but some cine-substitution occurs in the reaction of 3-chlorotropone with dimethylamine. Thermolysis and photolysis of 3- and 4-azidotropones gives the corresponding amino-derivatives as the only isolable products.