104849-58-3

Upstream product

• 765-03-7 1-dodecyne 
• 892-20-6 triphenylstannane 
• 109898-24-0 (Z)-1-tributylstannyl-1-dodecene 
• 97-94-9 triethyl borane 
• 75712-22-0 1-dodecenyl phenyl sulfide 

Downstream Products

• 75712-22-0 1-dodecenyl phenyl sulfide 
• 92740-99-3 (E)-1-triphenylgermyl-1-dodecene 
• 94074-97-2 [((Z)-Dodec-1-enyl)sulfanyl]-benzene 
• 94074-96-1 (E)-1-(phenylthio)-1-dodecene 

Relevant academic research and scientific papers

Isomerization of Olefins by Means of R3SnH-Et3B and Stereochemical Study on Reduction of Alkenyl Iodides

Isomerization of olefins with R3SnH-Et3B (R = Ph or n-Bu) system has been studied.Treatment of (Z)-1-triphenylstannyl-1-octene (1) or (E)-1-triphenylstannyl-1-octene (2) with a catalytic amount of Ph3SnH-Et3B provided an equilibrium mixture of 1/2 = 2/8.Partial isomerization was observed in the reaction of trivial alkenes such as 6-dodecene and 2,2-dimethyl-3-dodecene with R3SnH-Et3B system.Whereas (Z)- or (E)-6-dodecene was recovered unchanged upon treatment with n-Bu3SnH-Et3B at -78 deg C for 3 h, stirring a benzene solution of (Z)-6-dodecene, Ph3SnH, and Et3B at 60 deg C for 5 h gave an isomeric mixture of ()-6-dodecene and (E)-6-dodecene (Z/E = 64/36).Taking account of these results, the stereochemistry of the reduction of alkenyl iodides at -78 deg C with R3SnH-Et3B system was studied. 6-Dodecenyl radical proved to isomerize much more rapidly than it abstracts a hydrogen from R3SnH.

Application of Free Radical Substitution Reaction into Interconversion of 1-Alkenylsulfides, 1-Alkenylgermanes, and 1-Alkenylstannanes

Treatment of 1-alkenylsulfides or 1-alkenylstannanes with Ph3GeH in the presence of Et3B provides 1-alkenyltriphenylgermanes in good yields. 1-Alkenylstannanes are converted into 1-alkenylsulfides easily with PhSH-Et3B, whereas 1-alkenyltriphenylgermanes are recovered unchanged upon treatment with Ph3SnH-Et3B or PhSH-Et3B.

Palladium Catalyzed Hydrostannylation and Hydrogermylation of Acetylenes

Treatment of acetylenes with Ph3SnH or Ph3GeH in the presence of a catalytic amount of Pd(PPh3)4 provides the corresponding alkenyltriphenylstannanes or alkenyltriphenylgermanes in good yields.