3461-40-3

Upstream product

• 67-56-1 methanol 
• 530-48-3 1,1-Diphenylethylene 
• 40237-72-7 (2-methoxyethene-1,1-diyl)dibenzene 

Relevant academic research and scientific papers

Electrochemical Difunctionalization of Styrenes via Chemoselective Oxo-Azidation or Oxo-Hydroxyphthalimidation

Atom- and step-economic oxo-azidation and oxo-hydroxyphthalimidation of styrenes have been developed under mild electrolytic conditions, respectively. Various valuable alpha-azido or hydroxyphthalimide aromatic ketones were synthesized efficiently from readily available styrenes, azides, and N-hydroxyphthalimides. Mechanism studies show that two different pathways involved in these two transformations.

Substrate-Dependent Electrochemical Dimethoxylation of Olefins

A general and direct electrochemical dimethoxylation of olefins is reported, which enables a divergent route to different products depending on the structure of olefins. The present protocol features mild conditions and broad substrate scope (49 examples) obviating the usage of transtion-metals and external oxidants. More importantly, to rationalize the divergent route of the transformation, an ionic-like pathway involving carbocation intermediate is proposed and the diverse products is attributed to the different stability of carbocations. (Figure presented.).

The photochemistry of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenyiethene in methanol. Homolytic cleavage versus electron-transfer pathways

The photochemical reactivity of a series of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in a nucleophilic solvent (methanol) has been investigated. Analysis of the photochemical reactions involving the 4-halobenzonitriles revealed formation of alkene-methanol adducts, such as 1-methoxy-2,2-diphenylethane, 1-methoxy-2,2-diphenylethene, and 1,1-dimethoxy-2,2-diphenylethane, indicative of a photochemical electron-transfer mechanism. These products were not significant in the photochemical reactions involving the 4-haloanisoles. Both the 4-halobenzonitriles and the 4-haloanisoles produced an 'arene-alkene-methanol Markovnikov adduct, 1-aryl-2-methoxy-2,2-diphenylethane (aryl = 4-cyanophenyl or 4-methoxyphenyl). This compound was shown to undergo an acid-catalysed elimination to 1-aryl-2,2-diphenylethene under the reaction conditions, which subsequently underwent a 6π-electrocyclization to the 3-substituted(cyano or methoxy)-9-phenylphenanthrene. Possible mechanisms for the observed reactivity are discussed and evaluated.

Photochemical Electron-transfer Reaction between Aromatic Olefins and Metal Ions. Dependence of the Reaction Course on the Structure of the Olefins

To investigate the photochemical electron transfer from aromatic olefins to copper(II) or iron(III) ions, a series of substituted styrenes (1) was irradiated in the presence of copper(II) or iron(II) salts in methanol, which gave dimethoxylated monomers (2) and one or more of three types of dimethoxylated dimers .The formation of these products are reasonably attributed to the participation of hte cation radicals of the olefins generated by electron transfer from excited olefins to the methal ions.Substituents on the substrates are found to govern the reaction products.

ELECTROCHEMICAL OXIDATION OF AROMATIC OLEFINS. DEPENDENCE OF THE REACTION COURSE ON THE STRUCTURE OF THE OLEFINS AND ON THE NATURE OF THE ANODES

Anodic oxidation of a series of substituted styrenes was investigated in methanol with a platinum and a graphite electrode.Use of the platinum anode gave mainly dimethoxylated monomers accompanied wiht one or more of three types of dimethoxylated dimers (αα-, αβ-, and ββ-dimers) depending on the substituents.Use of the graphite anode, however, afforded the ββ-dimers as the main product together with dimethoxylated monomers.