Syntheses and structural analysis of 10-monoxy- and -dioxy-5-N-substituted iminothianthrene derivatives and the stereochemical change on their sulfur atom under acidic and thermal conditions.
5-(N-p)-Toluenesulfonyl)iminothianthrenes, whose sulfur atoms are oxidized to a sulfoxide or sulfone at the 10-position, were hydrolysed readily in high yield to N-unsubstituted-sulfilimines by using concentrated H2SO4. During hydrolysis, 10-monoxy-5-N-unsubstituted-sulfilimines were obtained as a separable mixture of the cis and trans isomers. The stereochemical interconversion of these compounds was studied under both hydrolytic and thermal conditions and their structures were elucidated by using X-ray crystallography.
Morita
H
H
Department of Chemical and Biochemical Engineering, Faculty of Engineering, Toyama University, Japan. morita@eng.toyama-u.ac.jp
Kawaguchi
H
H
Yoshimura
T
T
Tsukurimichi
E
E
Shimasaki
C
C
Horn
E
E