90030-12-9

Upstream product

• 100-39-0 benzyl bromide 
• 22702-77-8 1,2-dichlorotetramethyldigermane 
• 76054-64-3 7,7-dimethyl-1,4,5,6-tetraphenyl-2,3-benzo-7-germanorbornadiene 
• 1730-66-1 methylgermanium bromide 
• 4342-61-4 1,2-dichlorotetramethylsilane 

Downstream Products

• 1066-63-3 octamethyltrigermane 
• 14938-41-1 decamethyltetragermane 
• 2848-62-6 phenyl(trimethylgermyl)methane 
• 13189-68-9 Dodecamethyl-penta-n-german 
• 113352-21-9 PhCH₂GeMe₂Et 
• 94845-52-0 Et₂Me₆Ge₃ 

Relevant academic research and scientific papers

Palladium-Catalyzed Germylation of Organic Halides with a Digermane. Unexpected Formation of Germylene-Insertion Type Products

Organic halides (RX) underwent dehalogenative germylation and germylene insertion type reactions with ClMe2GeGeMe2Cl in the presence of Pd(PPh3)4 as catalyst to give RGeMe2Cl and RGeMe2X respectively.

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.

Insertion reactions of dimethylgermylene, Me2Ge, and their mechanisms as studied by CIDNP

The insertion of germylenes into carbon-halogen bonds is shown to occur, in the case of thermally generated Me2Ge and benzyl bromide, via a cage abstraction-recombination reaction, giving typical 1H CIDNP effects proving the singlet state of Me2Ge. Besides, an abstraction reaction of escaped ·GeMe2Br yields Me2GeBr2 also showing 1H CIDNP effects, followed by an one-step insertion of Me2Ge into Ge-Br bonds of Me2GeBr2, giving oligogermanes without 1H CIDNP effects.