14629-97-1

Upstream product

• 103-64-0 bromostyrene 
• 76054-64-3 7,7-dimethyl-1,4,5,6-tetraphenyl-2,3-benzo-7-germanorbornadiene 
• 113352-24-2 PhCHCHGeMe₂GeMe₃ 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 1066-37-1 trimethylbromogermane 
• 30094-01-0 (E)-(2-phenylethenyl)magnesium bromide 
• 622-25-3 1-(2-chlorovinyl)benzene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 993-52-2 hexamethyldigermane 

Relevant academic research and scientific papers

Palladium-Catalyzed Germylation of Aryl Bromides and Aryl Triflates Using Hexamethyldigermane

Palladium-catalyzed germylation of aryl bromides and aryl triflates using commercially available hexamethyldigermane is described. Optimized reaction conditions afforded various functionalized aryltrimethylgermanes, including drug-like molecules, in moderate to good yields, demonstrating the versatility of the presented protocols.

Photochemical Reactions of Vinyl-, Styryl- and Benzyl-Substituted Digermanes

Photochemical reactions of vinyl-, styryl- and benzyl-substituted digermanes by chemical trapping experiments.Photolysis of vinylpentamethyldigermane afforded 1-trimethyl-2-(pentamethyldigermyl)ethane as a major product, and styrylpentamethyldigermanes gave mainly styryltrimethylgermane.On the other hand, photolysis of benzyl-substituted digermanes (benzylpentamethyldigermane and 1,2-dibenzyltetramethyldigermane) gave hydrogermanes and hydrodigermanes as main products, respectively.These products were derived from germyl radicals generated by photoinduced homolysis of the germanium-germanium bond.In carbon tetra chloride (CCl4), these germyl radicals were converted to the corresponding chlorogermanes by abstraction of a chlorine atom.Germylene species were also to be evolved from such photolyses.

A First Palladium-Catalyzed Aryldegermylation of Styryltrimethylgermanes

Both β-(E)- and β-(Z)-styryltrimethylgermanes easily reacted with arenediazonium tetrafluoroborates under palladium catalysis to give aryldegermylated products, (E)-PhCH=CHAr and Ph(Ar)C=CH2.On the other hand, the aryldegermylation of α-styrylgermane gave (E)-stilbene derivates with high stereo- and regioselectivities.

Chemistry of heavy carbene analogues R2M (M = Si, Ge, Sn). 12. Concerted and nonconcerted insertion reactions of the germylene Me2Ge into the carbon-halogen bond

During the reaction of Me2Ge with CCl3X (X = Cl, Br), PhCH2X (X = Br, I), and Ph2CHCl, 1H CIDNP is observed in the products of net insertion of Me2Ge into the carbon-halogen bond and in Me2GeX2 (X = Cl, Br). It is concluded that a two-step radical reaction takes place by an abstraction-recombination mechanism. No reaction takes place with alkyl halides that have a C-X bond dissociation energy of more than about 70 kcal/mol. Me2Ge is generated thermally at 70-95°C or photochemically from the 7-germabenzonorbornadiene 1 and reacts in both cases in the singlet state. The activation energy for forming Me2Ge from 1 is 19 kcal/mol for the reaction with CCl4. Insertion products are also formed with the alkenyl halides CH2=CHCH2X, PhCH=CHX (X = Cl, Br), and 2-bromobut-2-ene, but without showing CIDNP effects. Since Me2GeX2 was not found either, Me2Ge reacts in these cases in a nonradical manner. It does not react with 1-chlorocyclohexene, but it does react with Me2GeX2 under formation of digermanes and/or oligogermanes without CIDNP.