A Contribution to the Study of the Constitution of the Hydroxyazo Compounds. The Action of Unsymmetrical Benzoylparatolylhydrazine Upon Benzoquinone and Its Homologs.

McPherson, William; Stratton, George W.

doi:10.1021/ja02169a020

Cited by 7 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3-Fluorophenylhydrazine hydrochloride was obtained from Koch-Light, Te02 from PCR Research Chemicals Inc. and 4-nitrophenyldiazonium tetrafluoroborate from Eastman. 4-Methylphenylhydrazine [9] and benzil monohydrazone [10] were synthesized according to the literature.…”

Section: CImentioning

confidence: 99%

Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO₂

Bergman

Engman

1980

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

show abstract

Section: CImentioning

confidence: 99%

Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO₂

Bergman

Engman

1980

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

show abstract

Replacement of the Aromatic Primary Amino Group by Hydrogen*National Research Fellow, 1942–1943. Present address, Purdue University.

Kornblum

2011

Organic Reactions

View full text Add to dashboard Cite

The replacement of an aromatic primary amino group by hydrogen is usually effected by the reduction of the diazonium salt derived from the amine. It is evident that the success of the deamination process is a function of the completeness of diazotization as well as of the reduction. Diazonium compounds have been treated with a great variety of reducing agents some of which have become incorporated into procedures for replacing the diazo group by hydrogen. The important process involve reduction by: alcohols, hypophosphorous acid, alkaline formaldehyde, stabilization of the diazonium salt with naphthalene‐1,5‐disulfonic acid followed by treatment with zinc or copper, sodium stannite, stannous chloride or sodium sulfate reduction to hydrazine from which the hydrocarbon is obtained by oxidation.

show abstract

Kinetics of Dissociative Electron Transfer to Ascaridole and Dihydroascaridole—Model Bicyclic Endoperoxides of Biological Relevance

Donkers

Workentin

2001

Chem. Eur. J.

View full text Add to dashboard Cite

The homogeneous and heterogeneous electron transfer (ET) reduction of ascaridole (ASC) and dihydroascaridole (DASC), two bicyclic endoperoxides, chosen as convenient models of the bridged bicyclic endoperoxides found in biologically relevant systems, were studied in aprotic media by using electrochemical methods. ET is shown to follow a concerted dissociative mechanism that leads to the distonic radical anion, which is itself reduced in a second step by an overall two-electron process. The kinetics of homogeneous ET to these endoperoxides from an extensive series of radical anion electron donors were measured as a function of the driving force of electron transfer (deltaG(o)ET). The kinetics of heterogeneous ET were also studied by convolution analysis. Together, the heterogeneous and homogeneous ET kinetic data provide the best example of the parabolic nature of the activation-driving force relationship for a concerted dissociative ET described by Savéant; the data is particularly illustrative due to the low bond-dissociation enthalpy (BDE) of the O-O bond and hence small intrinsic barriers. Analysis of the data allowed the dissociative reduction potentials (E(o)diss) to be determined as -1.2 and -1.1 Vagainst SCE for ASC and DASC, respectively. Unusually low pre-exponential factors measured in temperature-dependent kinetic studies suggest that ET to these O-O bonded systems is nonadiabatic. Analysis of ET kinetics for ASC and DASC by the Savéant model with a modification for nonadiabaticity allowed the intrinsic free energy for ET to be determined. The use of this approach and estimates for the BDE provide approximations of the reorganization energies. We suggest the methodology described herein can be used to evaluate the extent of ET to other endoperoxides of biological relevance and to provide thermochemical data not otherwise available.

show abstract

A Contribution to the Study of the Constitution of the Hydroxyazo Compounds. The Action of Unsymmetrical Benzoylparatolylhydrazine Upon Benzoquinone and Its Homologs.

Cited by 7 publications

References 0 publications

Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO₂

Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO₂

Replacement of the Aromatic Primary Amino Group by Hydrogen*National Research Fellow, 1942–1943. Present address, Purdue University.

Kinetics of Dissociative Electron Transfer to Ascaridole and Dihydroascaridole—Model Bicyclic Endoperoxides of Biological Relevance

Contact Info

Product

Resources

About

A Contribution to the Study of the Constitution of the Hydroxyazo Compounds. The Action of Unsymmetrical Benzoylparatolylhydrazine Upon Benzoquinone and Its Homologs.

Cited by 7 publications

References 0 publications

Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO2

Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO2

Replacement of the Aromatic Primary Amino Group by Hydrogen*National Research Fellow, 1942–1943. Present address, Purdue University.

Kinetics of Dissociative Electron Transfer to Ascaridole and Dihydroascaridole—Model Bicyclic Endoperoxides of Biological Relevance

Contact Info

Product

Resources

About

Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO₂

Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO₂