80784-19-6

Usage

General Description

1,3-Benzodioxole,5,5'-(1,2-ethanediyl)bis- is a chemical compound that is also known as ethylene glycol dibenzoate. It is a colorless to pale yellow liquid with a fruity odor. 1,3-Benzodioxole,5,5'-(1,2-ethanediyl)bis- is commonly used as a plasticizer in various industrial applications, including in the production of resins, adhesives, and coatings. It works by softening and increasing the flexibility of the materials it is added to. However, it is important to handle this chemical with caution, as it can be harmful if swallowed or inhaled and may cause skin and eye irritation. Proper safety measures and handling procedures should be followed when working with 1,3-Benzodioxole,5,5'-(1,2-ethanediyl)bis-.

Upstream product

• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 100-58-3 phenylmagnesium bromide 
• 591-50-4 iodobenzene 

Downstream Products

• 3842-68-0 4,4'-(ethane-1,2-diyl)dibenzene-1,2-diol 

Relevant academic research and scientific papers

Mechanistic Characterization of (Xantphos)Ni(I)-Mediated Alkyl Bromide Activation: Oxidative Addition, Electron Transfer, or Halogen-Atom Abstraction

Ni(I)-mediated single-electron oxidative activation of alkyl halides has been extensively proposed as a key step in Ni-catalyzed cross-coupling reactions to generate radical intermediates. There are four mechanisms through which this step could take place: oxidative addition, outer-sphere electron transfer, inner-sphere electron transfer, and concerted halogen-atom abstraction. Despite considerable computational studies, there is no experimental study to evaluate all four pathways for Ni(I)-mediated alkyl radical formation. Herein, we report the isolation of a series of (Xantphos)Ni(I)-Ar complexes that selectively activate alkyl halides over aryl halides to eject radicals and form Ni(II) complexes. This observation allows the application of kinetic studies on the steric, electronic, and solvent effects, in combination with DFT calculations, to systematically assess the four possible pathways. Our data reveal that (Xantphos)Ni(I)-mediated alkyl halide activation proceeds via a concerted halogen-atom abstraction mechanism. This result corroborates previous DFT studies on (terpy)Ni(I)- and (py)Ni(I)-mediated alkyl radical formation, and contrasts with the outer-sphere electron transfer pathway observed for (PPh3)4Ni(0)-mediated aryl halide activation. This study of a model system provides insight into the overall mechanism of Ni-catalyzed cross-coupling reactions and offers a basis for differentiating electrophiles in cross-electrophile coupling reactions.