Abstract
Highly efficient stereoselective syntheses of novel bis(E-2-chlorovinyl) selenides and bis(E-2-bromovinyl) selenides in quantitative yields by reactions of selenium dichloride and dibromide with alkynes were developed. The reactions proceeded at room temperature as anti-addition giving products exclusively with (E)-stereochemistry. The glutathione peroxidase-like activity of the obtained products was estimated and compounds with high activity were found. The influence of substituents in the products on their glutathione peroxidase-like activity was discussed.
Highlights
The term “click chemistry” was coined by K
The stereoselective syntheses of novel bis(E-2-chlorovinyl) and bis(E-2-bromovinyl) selenides in quantitative yields by electrophilic addition reactions of selenium dichloride and selenium dibromide to dialkylacetylenes were developed
The reactions can be regarded as selenium dihalides click chemistry due to the quantitative yields and 100% stereoselectivity
Summary
The term “click chemistry” was coined by K. Bis(E-2-chloro-1-ethyl-1-butenyl) selenide [5] was obtained under the same conditions as compound 4 from selenium dichloride and 3-hexyne as a light yellow oil in quantitative yield. Bis(E-2-chloro-1-butyl-1-hexenyl) selenide [7] was obtained under the same conditions as compound 4 but for 2 h from selenium dichloride and 5-decyne as a light yellow oil in quantitative yield. Bis(E-2-bromo-1-ethyl-1-butenyl) selenide [9] was obtained under the same conditions as compound 8 but for 2 h from selenium dibromide and 3-hexyne as a light yellow oil in quantitative yield. Bis(E-2-bromo-1-propyl-1-pentenyl) selenide [10] was obtained under the same conditions as compound 8 but for 2 h from selenium dibromide and 4-octyne as a light yellow oil in quantitative yield. Bis(E-2-bromo-1-butyl-1-hexenyl) selenide [11] was obtained under the same conditions as compound 8 but for 3 h from selenium dibromide and 5-decyne as a light yellow oil in quantitative yield. Found: C 46.34, H 7.00, Br 30.89, Se 15.45%
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