Title of article :
Substituent Effects on [1,3]-Rearrangement of Alkynyl S,N-Acetals to 1-Amino-3-Sulfenylallenes and their Conversion to α,β-Unsaturated Ketones
Author/Authors :
Murai, Toshiaki Gifu University - Faculty of Engineering - Department of Chemistry, Japan , Mutoh, Yuichiro Gifu University - Faculty of Engineering - Department of Chemistry, Japan , Fukushima, Kozue Gifu University - Faculty of Engineering - Department of Chemistry, Japan
Abstract :
The reaction of thioiminium salts derived from aromatic thioamides with lithium phenylacetylide exclusively gave S,N-acetals, whereas the reaction with lithium (trimethylsilyl)acetylide gave 1-amino-3-sulfenylallenes via [1,3]-rearrangement. The easiness of [1,3]-rearrangement was highly dependent on the substituents at the nitrogen atom. Chromatographic purification of the reaction mixture produced α,β-unsaturated ketones.
Keywords :
Thioamides , alkynyl S , N , acetals , [1 , 3] , rearrangement , 1 , amino , 3 , sulfenylallenes , substituent effects , a , b , unsaturated ketones.
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
