Ethers benzyl phenyl

The first reaction probably involving attack by benzyl radicals on a heterocyclic system was reported by Hickinbottom. - He found that, when benzyl phenyl ether is heated in quinoline to about 250 C, benzylquinoline and hydroxyphenylquinolines are the main products. 

How could you prepare benzyl phenyl ether from benzene and phenol More than one step is required. 

Tarbell and Petropoulos159 measured the rate of formation of phenol from benzyl phenyl ether catalysed by aluminium bromide and found it to be a first-order process. Moreover, the rate coefficient was the same as that for the formation of phenol from ortho benzyl phenol. Since the ratio of products (phenol ortho benzyl phenol) was unaffected by a large change in the temperature it was argued... 

As shown in Table IV, all phenols tested were confirmed to accelerate the conversion of phenyl benzyl ether. In this thermolysis, benzyl phenyl ether was decomposed to toluene and phenol (ca. 60%) and also isomerized to benzyl phenol (ca. 40%). 

In some model compound studies with the i-PrOH/KOH system we found that anthracene was converted to 9,10-dihydroanthracene in 64% yield. Benzyl phenyl ether was also studied and was converted to a polymeric material under the reaction conditions. There were no traces of phenol nor toluene, the expected reduction products. 

Note. In a recent paper, Miller and Stein have provided values for both C-C and C-0 bonds for a variety of coal model compounds, including bibenzyl and benzyl phenyl ether (11). Their rate constant for bibenzyl provides half-life values at 335°C and 400°C even larger than those discussed here, and it would seem on the basis of their data that at those low temperatures C-C scission in bibenzyl itself is too slow for thermal scission to be significant. 

One of the first kinetic studies of the fragmentation of a C—O bond in an ether radical anion was reported by Maslak and Guthrie. " In this study substituted benzyl phenyl ethers (as well as some other benzyl-type phenyl ethers) were treated with 2,4,6-tri-tert-butylnitrobenzene radical anion to produce ArCH20Ph or PhCH20Ar and the unimolecular decay of the anion radical was monitored using EPR. Despite some discrepancies between the values of the reported rate constants, ... 

Sn2 reaction of phenoxide with benzyl chloride to afford benzyl phenyl ether. 

The yield of diphenyl ether is approximately one-tenth that of benzyl phenyl ether and allyl phenyl ether (185). 

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