Recyclization of S- and N-Containing Cyclic Peroxides with Aromatic Amines.

Recyclization of tetraoxathiaspiroalkanes and tetraoxathiocanes with primary amines (2- and 4-fluoroanilines, 3- and 4-chloroanilines, 2-methylaniline, 2- and 4-methoxyanilines, ammonium chloride) in the presence of samarium(III) nitrate hexahydrate afforded the corresponding cyclic azadiperoxides. N-(tert-Butyl)hexaoxaazadispirocycloalkanes underwent similar recyclization with 2-chloroaniline. The rate of the recyclization process depended on the nature of the heteroatom in the diperoxide ring (S > N > O). [ABSTRACT FROM AUTHOR]