Phenylethylene carbonate

Besides VC, vinyl ethylene carbonate (VEC), phenylethylene carbonate (PhEC), ° phenylvinylene carbonate (PhVC), catechol carbonate (CC), - ally methyl carbonate (AMC), - allyl ethyl carbonate (AEC), vinyl acetate (VA), and other vinyl compounds, - - acryronitrile (AAN) - and 2-cyanofuran (CN-F), whose chemical structures are given in Fig. 4.10, showed the similar effect and no graphite exfoliation in PC solvent systems. 

The LUMO of phenylethylene also has most density at the terminal (beta) carbon, so that these two atoms attach to each other, yielding the sterically unfavorable product. 

Staudinger and Pfenninger long ago suggested that addition of sulfur dioxide to diphenylketene gives an intermediate, 3,3-diphenyl-l,2-oxathietane-4-one 2-oxide, that decomposes to diphenylsulfene and carbon dioxide, the former yielding tetra-phenylethylene. Similar intermediates were proposed for the addition of sulfur dioxide to pentamethyleneketene, ketenimines, " ethylene, 1,1-difluoro-ethylenes, and an aluminum trichloride derivative of the 1,2,3,4-tetramethyl-cyclobutene cation. An intermediate adduct 494 actually has been isolated at... 

Takuwa and his coworkers have demonstrated that the irradiation of the aromatic carbonyl compounds (120) in the presence of the stannanes (121) affords the unsaturated alcohols (122) as the principal products. An electron transfer mechanism is proposed. Electron transfer is also involved in the reaction of amines with alkenes such as the phenylethylenes (123). The electron transfer in this instance affords an alkenyl radical anion the presence of which has been demonstrated by a variety of techniques. A further reaction has been uncovered in the photoreaction of, for example, the alkene (123a) with iV, AT-diethylani lino in the presence of carbon dioxide. This treatment affords the three carboxylated derivatives (124), (125), and (126) by trapping of the radical anion by carbon dioxide. Similar carboxylation was demonstrated for (123b) and biphenyleno. The influence of the amine on the yield of product was studied. ... 

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