1955
DOI: 10.1021/ja01620a022
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p-Methylbenzyl Hydroperoxide

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Cited by 22 publications
(11 citation statements)
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“…This tertiary carbon is much more susceptible to oxidation than primary carbons under similar conditions. Secondary carbons, such as for the ethylbenzene also show this susceptibility [18].…”
Section: Resultsmentioning
confidence: 94%
“…This tertiary carbon is much more susceptible to oxidation than primary carbons under similar conditions. Secondary carbons, such as for the ethylbenzene also show this susceptibility [18].…”
Section: Resultsmentioning
confidence: 94%
“…The reactions of benzylic oxidation were performed by passing air at the rate of 1 mL/min through 37 mg of a catalyst, suspended in 5 mL of p-xylene, and 0.3 mL of cyclohexene under reflux for 24 h. After addition of 10 ml of hexane, the catalyst was removed by filtration. The filtrate was concentrated in vacuum and the residue was analyzed by non-overlapping 1 H NMR signals, characteristic for the hydroperoxide 1 [16] (singlet at 4.95 ppm), alcohol 7 [17] (singlet at 4.60 ppm), aldehyde 8 [18] (singlet at 9.95 ppm), acid 2 [19] (doublet at 8.0 ppm), ester 9 [20] (singlet at 5.30 ppm), ether 10 [21] (singlet at 4.50 ppm), and hydrocarbon 11 [22] (singlet at 3.85 ppm).…”
Section: Experimental Partmentioning
confidence: 99%
“…The intermediate hydroperoxides formed in both cases ~vould be thermally decomposed to the aldehyde and alcohol. Lorand and Edwards (14) have, for example, prepared fi-inethylbenzyl hydroperoxide and find it rapidly decomposes above 130 O C . In reactions studied by Rust and T~aughan, a significant side reaction is the formation of the benzyl bron~ide; however, in the aqueous system, as pointed out by R'IcIntyre and Ravens (13), any bromides fornled would be rapidly hydrol~rzed t o the alcohol and subsequently oxidized to the acid under the reaction conditions.…”
Section: Time Of [Co++]mentioning
confidence: 99%
“…Secondly, cobalt(I1) must also have the ability of preventing bromine from being consumed by reactions such as [14] and [15]. Since the above equilibriuin is shifted to the right, the concentration of free hydrogen bromide will be low and, thus, the concentration of bromine atoms will be low.…”
Section: Time Of [Co++]mentioning
confidence: 99%
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