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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
Author(s) -
Morita Hiroyuki,
Kawaguchi Hiroyuki,
Yoshimura Toshiaki,
Tsukurimichi Eiichi,
Shimasaki Choichiro,
Horn Ernst
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20001103)6:21<3976::aid-chem3976>3.0.co;2-5
Subject(s) - chemistry , hydrolysis , sulfoxide , sulfur , sulfone , yield (engineering) , medicinal chemistry , organic chemistry , materials science , metallurgy
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 H 2 SO 4 . 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.