94789-35-2

Upstream product

• 37434-59-6 dimethyl 2-phenylmalonate 
• 74-86-2 acetylene 
• 101-41-7 benzeneacetic acid methyl ester 
• 591-50-4 iodobenzene 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 86735-66-2 methyl trans-4-bromotetrahydro-3-phenyl-2-oxo-3-furancarboxylate 
• 86735-66-2 methyl cis-4-bromotetrahydro-3-phenyl-2-oxo-3-furancarboxylate 
• 117111-79-2 dimethyl (1,2-dibromoethyl)phenylpropanedioate 

Relevant academic research and scientific papers

Radical Addition Enables 1,2-Aryl Migration from a Vinyl-Substituted All-Carbon Quaternary Center

An efficient method for photocatalytic perfluoroalkylation of vinyl-substituted all-carbon quaternary centers involving 1,2-aryl migration has been developed. The rearrangement reactions use fac-Ir(ppy)3, visible light and commercially available fluoroalkyl halides and can generate valuable multisubstituted perfluoroalkylated compounds in a single step that would be challenging to prepare by other methods. Mechanistically, the photoinduced alkyl radical addition to an alkene leads to the migration of a vicinal aryl substituent from its adjacent all-carbon quaternary center with the concomitant generation of a C-radical bearing two electron-withdrawing groups that is further reduced by a hydrogen donor to complete the domino sequence.

SOME REMARKS ON THE SEEFELDER METHOD OF VINYLATION OF CH-ACIDS

The relative reactivity sequence: PhCH(CN)COOMe > PhCH(CN)COOEt >> PhCH(COOMe)2 > n-BuCH(COOMe)2 > (Me)2CHCH(COOMe)2, for cadmium stearate catalyzed reactions of these CH-acids with acetylene has been established.Different catalytic efficiency of zinc and cadmium stearate towards particular kinds of CH-acids has been revealed.The usefulness of cadmium stearate for vinylation of monosubstituted acetoacetic esters has been demonstrated.