Halophenyl Oxalates.

Baker, J. W.; Schumacher, Ignatius.

doi:10.1021/je60023a034

Cited by 6 publications

(4 citation statements)

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“…6a and 6b were synthesized easily by dropping the corresponding alcohol in excess oxalyl chloride. Aryl chloroformylformates were reported ,, to use phenol or phenolate reacting with oxalyl chloride in the presence of a base at room temperature. However, when these methods were applied to our substrates, either the reactions failed or the conversion was poor.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Structure, and Acaricidal/Insecticidal Activity of Novel Spirocyclic Tetronic Acid Derivatives Containing an Oxalyl Moiety

Liu

Lei

et al. 2011

J. Agric. Food Chem.

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A series of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety was designed and synthesized via the key intermediate 3-(2,4,6-trimethyl)-2-oxo-1-oxaspiro[4.4]-decyl-3-en-4-ol. The target compounds were identified by (1)H NMR and elemental analysis or high-resolution mass spectrum (HRMS). The results of bioassays indicated that most of the target compounds possessed excellent acaricidal activities against carmine spider mite larvae and eggs. Especially, diisopropylamino oxalyl compound 7g and piperidine oxalyl compound 7h were 1.4- and 2.3-fold as high as the activities of commercial Spiromesifen, respectively, against spider mite eggs. Moreover, most of the target compounds exhibited insecticidal activities against Lepidoptera pest. Interestingly, compounds containing alkylamino-substituted oxalyl moiety showed obvious selectivity between spider mite larvae and eggs because the activities against spider mite eggs of 7g and 7h were 25-fold those against spider mite larvae, whereas Spiromesifen had no significant differences in these activities. This meant that the introduction of an oxalyl moiety to spirocyclic tetronic acid might lead to novel biological activity characteristics.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Structure, and Acaricidal/Insecticidal Activity of Novel Spirocyclic Tetronic Acid Derivatives Containing an Oxalyl Moiety

Liu

Lei

et al. 2011

J. Agric. Food Chem.

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“…Normalized spectral sensitivity curve Baker and Schumacher (1964). Sodium salicylate (BDH Analar) was used without further purification.…”

Section: Methodsmentioning

confidence: 99%

“…(Bis-(pentachlorophenyl) oxalate (PCPO) was prepared following the general method of Rauhut (Rauhut et al, 1967) Wavenumber v I lo3 cm ' Figure. 3. Normalized spectral sensitivity curve Baker and Schumacher (1964). Sodium salicylate (BDH Analar) was used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Determination of absolute chemiluminescence quantum yields for reactions of bis‐(pentachlorophenyl) oxalate, hydrogen peroxide and fluorescent compounds

Catherall

Palmer

Cundall

1989

J. Biolumin. Chemilumin.

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Absolute chemiluminescence quantum yields (phi CL) for reactions of bis-(pentachlorophenyl) oxalate (PCPO), hydrogen peroxide (H2O2) and 9:10 diphenyl anthracene (DPA) have been determined. A fully corrected chemiluminescence monitoring spectrometer was calibrated for spectral sensitivity using the chemiluminescence of the bis-(pentachlorophenyl) oxalate system as a liquid light source, the total photon output of which had previously been determined by chemical actinometry. At high (PCPO)/(H2O2) ratios phi CL was found to be independent of PCPO and H2O2 concentrations.

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“…The signal at -128.2 ppm was assigned to the half ester C based upon the following evidence. The acid chloride E, prepared by a procedure similar to tha: used for other haloaryl oxalates (Baker and Schumacher, 1964), showed a resonance at -127.2 ppm. On addition of water to the acid chloride E, a resonance due to the half ester C appeared at -128.2 ppm.…”

Section: Resultsmentioning

confidence: 99%

Oxalate/hydrogen peroxide chemiluminescence reaction. A ¹⁹F NMR probe of the reaction mechanism

Chokshi

Barbush

Carlson

et al. 1990

Biomedical Chromatography

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The mechanism of the oxalate/hydrogen peroxide chemiluminescence reaction has been examined by magnetic resonance techniques. Investigation of the reactive intermediates involved in chemiluminescence was carried out with bis(2,6-difluorophenyl)oxalate (DFPO) using 19F NMR to probe its reactions with aqueous hydrogen peroxide. Formation and reactions of the intermediate hydroperoxy oxalate ester B along with the formation of the half ester product C and difluorophenol D were monitored by 19F NMR. When the reaction of DFPO and aqueous hydrogen peroxide was carried out in the presence of dansylphenylalanine, a typical fluorescent analyte, the intensity of the resonance due to the intermediate B was diminished in direct proportion to the concentration of the analyte. Comparison of the time/intensity profile of the chemiluminescence emission with that of the 19F NMR transient suggests that the hydroperoxy oxalate ester B is the likely 'reactive' intermediate, capable of participating in a chemically initiated electron exchange luminescence mechanism.

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Halophenyl Oxalates.

Cited by 6 publications

References 0 publications

Design, Synthesis, Structure, and Acaricidal/Insecticidal Activity of Novel Spirocyclic Tetronic Acid Derivatives Containing an Oxalyl Moiety

Design, Synthesis, Structure, and Acaricidal/Insecticidal Activity of Novel Spirocyclic Tetronic Acid Derivatives Containing an Oxalyl Moiety

Determination of absolute chemiluminescence quantum yields for reactions of bis‐(pentachlorophenyl) oxalate, hydrogen peroxide and fluorescent compounds

Oxalate/hydrogen peroxide chemiluminescence reaction. A ¹⁹F NMR probe of the reaction mechanism

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Halophenyl Oxalates.

Cited by 6 publications

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Design, Synthesis, Structure, and Acaricidal/Insecticidal Activity of Novel Spirocyclic Tetronic Acid Derivatives Containing an Oxalyl Moiety

Design, Synthesis, Structure, and Acaricidal/Insecticidal Activity of Novel Spirocyclic Tetronic Acid Derivatives Containing an Oxalyl Moiety

Determination of absolute chemiluminescence quantum yields for reactions of bis‐(pentachlorophenyl) oxalate, hydrogen peroxide and fluorescent compounds

Oxalate/hydrogen peroxide chemiluminescence reaction. A 19F NMR probe of the reaction mechanism

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Oxalate/hydrogen peroxide chemiluminescence reaction. A ¹⁹F NMR probe of the reaction mechanism