1960
DOI: 10.1021/ja01491a027
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Concerning the Mechanism of the Reduction of Hydroperoxides by Trisubstituted Phosphines and Trisubstituted Phosphites1

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Cited by 72 publications
(30 citation statements)
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“…Several experiments with NEt 3 and tert-butylmercaptan [20] showed occasionally either over-oxidation compounds or complete inhibition of the O 2 oxidation reaction. After extensive experimentation, we found that dibutyl sulfide or triphenylphosphine [21] can efficiently prevent over-oxidation through peroxide reduction without hampering the desired reaction. The reaction conditions in the presence or absence of a reducant were tested for the entire selected series of amino acid derivatives (Table 1).…”
Section: Resultsmentioning
confidence: 99%
“…Several experiments with NEt 3 and tert-butylmercaptan [20] showed occasionally either over-oxidation compounds or complete inhibition of the O 2 oxidation reaction. After extensive experimentation, we found that dibutyl sulfide or triphenylphosphine [21] can efficiently prevent over-oxidation through peroxide reduction without hampering the desired reaction. The reaction conditions in the presence or absence of a reducant were tested for the entire selected series of amino acid derivatives (Table 1).…”
Section: Resultsmentioning
confidence: 99%
“…Since this phenyl glycol crystack of TPP to the more electro-positive hydroxyl tallized into fine needle-shaped crystals, it was oxygen. 16 This mechanism was proved by Davies assumed to be optically pure. Interestingly the et al 17 who showed that optically active a-phe-1 H-NMR spectrum of this sample of phenyl glycol nylethyl hydroperoxide is reduced by TPP with matches with the spectrum of (/)-(S)-phenyl complete retention of configuration to a-phenyethane-1,2-diol reported in the literature.…”
Section: Mechanism Of the Reactionmentioning
confidence: 90%
“…The reduction of hydroperoxides by trisubstituted phosphines has been shown to be highly specific. 33,34 The TPPO produced can be quantified using RPLC. 35 Figure 4 shows that after 2 h the reaction was complete with matching TPPO and H 2 O 2 concentrations.…”
Section: Hydroperoxide Quantitationmentioning
confidence: 99%