Aminolysis of 2,4-Dinitrophenyl and 3,4-Dinitrophenyl Diphenylphosphinothioates: Steric Hindrance versus Nucleofugality in Nucleophilic Substitution Reactions
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چکیده
منابع مشابه
Mechanisms of nucleophilic substitution reactions of methylated hydroxylamines with bis(2,4-dinitrophenyl)phosphate. Mass spectrometric identification of key intermediates.
Mono- and dimethylation of hydroxylamine on nitrogen does not significantly affect rates of initial attack of NHMeOH and NMe(2)OH on bis(2,4-dinitrophenyl)phosphate (BDNPP), which is largely by oxygen phosphorylation. O-Methylation, however, blocks this reaction and NH(2)OMe then slowly reacts with BDNPP via N-attack at phosphorus and at the aryl group. With NHMeOH, the initial product of O-att...
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The reaction between the benzohydroxamate anion (BHO(-)) and bis(2,4-dinitrophenyl)phosphate (BDNPP) has been examined kinetically, and the products were characterized by mass and NMR spectroscopy. The nucleophilic attack of BHO(-) follows two reaction paths: (i) at phosphorus, giving an unstable intermediate that undergoes a Lossen rearrangement to phenyl isocyanate, aniline, diphenylurea, and...
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Previous work has shown that the peptide-like growth factor strepogenin probably occurs in certain proteins such as insulin and trypsinogen at the amino end of the protein (l), and that it is liberated by suitable enzymic digestion. This conclusion suggested a means for attacking the almost insurmountable task involved in separating the one compound strepogenin from the mixture of numerous pept...
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The 2,3,4-tri-toluenesulfonate ester derivatives of the methyl pyranosides of l-arabinose, d-ribose, d-lyxose, and d-xylose have been prepared, and their substitution reactions with various nucleophiles have been examined. For arabinose, xylose, and ribose, highly regioselective monosubstitutions were observed with benzoate, nitrite, and azide anions. These reactions have led to short and simpl...
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Numerous dinitrophenyl amino acid preparations injected intradermally induced contact hypersensitivity to dinitrochlorobenzene, delayed type skin reactions to DNP-amino acids, and anti-DNP antibodies in guinea pigs. Some DNP-amino adds induced precipitating anti-DNP antibodies in rabbits as well. Some of the DNP-ammo acids studied were regularly immunogenic, possible immunogenic impurities havi...
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ژورنال
عنوان ژورنال: Bulletin of the Korean Chemical Society
سال: 2011
ISSN: 0253-2964
DOI: 10.5012/bkcs.2011.32.6.2117