95887-36-8

Upstream product

• 1119-64-8 1-bromohexyne 
• 1119-67-1 1-iodo-1-hexyne 
• 4440-01-1 lithium phenylacetylide 
• 95887-55-1 Bis-(1,2-dimethyl-propyl)-((E)-1-phenylethynyl-hex-1-enyl)-borane 
• 106-95-6 allyl bromide 

Relevant academic research and scientific papers

REGIO- AND STEREOSPECIFIC SYNTHESIS OF TRIPLY UNSATURATED HYDROCARBONS FROM INTERNAL ENYNYLDIALKYLBORANES

Internal enynyldialkylboranes give regio- and stereospecifically designed conjugated enynes, bearing an allyl or 1-alkynyl group on the internal alkenyl carbon atom, by a coupling reaction with allyl bromide or 1-bromo-1-alkynes.

The Synthesis of Internal Conjugated (E)-Enynyldialkylboranes and Their Applications to the Syntheses of Conjugated Alkynones, Conjugated (E)-Enynes, and Conjugated Enynes Bearing an Unsaturated Group on the Double Bond

Internal conjugated (E)-enynyldialkylboranes were synthesized by successive reactions of 1-iodo-1-alkynes with dialkylboranes and 1-alkynyllithiums in 31-79percent yields. (E)-Enynyldialkylboranes, thus obtained, gave regio- and/or stereospecifically defined corresponding conjugated alkynones by alkaline hydrogen peroxide oxidation, conjugated (E)-enynes by protonolysis with acetic acid, and conjugated enynes bearing an unsaturated group on the internal alkenyl carbon atom by bis(acetylacetonato)copper-catalyzed cross-coupling reaction with allyl bromide or 1-bromo-1-hexyne respectively.