37920-24-4

Upstream product

• 20651-71-2 4-butyl benzoic acid 
• 75-24-1 trimethylaluminum 
• 28788-62-7 4-butylbenzoyl chloride 
• 1350927-23-9 triallyl(phenyl)germane 
• 20651-67-6 4-butyliodobenzene 

Relevant academic research and scientific papers

3D-Printing inside the Glovebox: A Versatile Tool for Inert-Gas Chemistry Combined with Spectroscopy

3D-Printing with the well-established 'Fused Deposition Modeling' technology was used to print totally gas-tight reaction vessels, combined with printed cuvettes, inside the inert-gas atmosphere of a glovebox. During pauses of the print, the reaction flasks out of acrylonitrile butadiene styrene were filled with various reactants. After the basic test reactions to proof the oxygen tightness and investigations of the influence of printing within an inert-gas atmosphere, scope and limitations of the method are presented by syntheses of new compounds with highly reactive reagents, such as trimethylaluminium, and reaction monitoring via UV/VIS, IR, and NMR spectroscopy. The applicable temperature range, the choice of solvents, the reaction times, and the analytical methods have been investigated in detail. A set of reaction flasks is presented, which allow routine inert-gas syntheses and combined spectroscopy without modifications of the glovebox, the 3D-printer, or the spectrometers. Overall, this demonstrates the potential of 3D-printed reaction cuvettes to become a complementary standard method in inert-gas chemistry.

Cascade radical cyclizations via biradicals generated from (Z)-1,2,4-heptatrien-6-ynes

On heating in refluxing benzene, acyclic enyne-allene 4 underwent intramolecular transformations in a sequence with an initial Myers cycloaromatization to form α,3-didehydrotoluene biradical 5 followed by a 5-exo cyclization of the benzenoid radical cente

Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe3

Bidentate phosphine-assisted methylenation of acyl fluorides and acyl chlorides with substituted with aryl, alkenyl, and alkyl groups trimethylaluminum afforded an array of 2-substituted propene derivatives. The addition of a catalytic amount of DPPM increased an efficiency of the reactions. Trimethylaluminum as the methylenation reagent not only eliminates the presynthesis of methylene transfer reagent, but provides an efficient method for the synthesis of a series of 2-substituted propenes.

Chemoselective transfer of allyl or phenyl group from allyl(phenyl)germanes in Pd-catalyzed reactions with aryl halides

Treatment of chloro(phenyl)germanes with allylmagnesium bromide yielded allyl(phenyl)germanes. Coupling of the allyl- (phenyl)germanes with aryl halides in 1,4-dioxane in the presence of aqueous NaOH and Pd catalyst resulted in Heck-type transfer of the allyl group providing the corresponding allylated aryls. On the other hand, reaction of allyl(phenyl)germanes with SbF5 intercalated in graphite in toluene and subsequent treatment of the resulting germanyl fluorides with TBAF generates reactive hypervalent fluorogermanates that undergo Stille-like Pd-catalyzed cross-coupling with aryl halides in wet toluene to provide biaryls.