The stereospecific oxidation of saturated secondary alcohol with dichlorodicyanoquinone

Iwamura, Junichi; Hirao, Nenokichi

doi:10.1016/s0040-4039(01)96173-8

Cited by 18 publications

(6 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a powerful oxidizing reagent in organic chemistry, DDQ has been proven to be useful for a wide range of reactions,6 such as oxidation of hydroaromatic compounds,7a steroid derivatives (ketones, pyrrazoles, lactones, etc. ),7b alcohols,7c phenols,7d allylic and benzylic ethers,7e and heterocyclic compounds 7f. Additionally, 1,4‐benzoquinones are good dienophiles for the DA reaction 8.…”

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

Voltammetric Determination of Pb, Cu and Hg in Biodiesel Using Gold Screen‐printed Electrode: Comparison of Batch‐injection Analysis with Conventional Electrochemical Systems

et al. 2015

View full text Add to dashboard Cite

This article compares the use of batch‐injection analysis (BIA) with a conventional batch system for the anodic stripping voltammetric (ASV) determination of Pb, Cu and Hg in biodiesel using screen‐printed gold electrode (SPGE). The optimized BIA conditions were 200 µL of injection volume of the digested samples at 5 µL s−1 directly on the working electrode of the SPGE immersed in 0.1 mol L−1 HCl solution. Therefore, BIA‐ASV presented the advantages of low sample consumption, which extended the SPGE lifetime to a whole working day of analyses, and potential for on‐site analysis using battery‐powered micropipettes and potentiostats. Although presenting lower sensitivity than conventional systems, the BIA‐ASV presented detection limit values of 1.0, 0.5 and 0.7 µg L−1, respectively for Pb, Cu and Hg, a linear range between 20 and 280 µg L−1, and adequate recovery values (90–110 %) for spiked biodiesel samples.

show abstract

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

Voltammetric Determination of Pb, Cu and Hg in Biodiesel Using Gold Screen‐printed Electrode: Comparison of Batch‐injection Analysis with Conventional Electrochemical Systems

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Furthermore, we observed a significant formation of this compound if 2-methoxy-3-methylhydroquinone (in ether) was admixed with 2-methoxy-3-methyl-1,4-benzoquinone (in ether) and kept at room temperature for about 1~2 days. Oxidative properties of benzoquionones such as dichlorodicyanoquionone (DDQ) are well known (Iwamura & Hirao 1973;Lewis & Paul 1981). As shown in Scheme 1, a cyclodehydrogenation of 2-methoxy-3-methyl-1,4-benzoquinone leads to the formation of 2-methoxy-3-methylhydroquinone (Brown & Jackman 1960;Creighton & Jackman 1960) Scheme 1…”

Section: Identification Of 2-methyl-34-methylenedioxyphenolmentioning

confidence: 99%

Hydroquinones from defensive secretion of a giant Pacific millipede, Acladocricus setigerus (Diplopoda: Spirobolida)

Buden

Attygalle

2007

Chemoecology

View full text Add to dashboard Cite

The presence of considerable quantities of hydroquinones including hydroquinone, 2-methylhydroquinone, 2,3-dimethoxyhydroquinone, 2-methoxy-3-methylhydroquinone, and 2,3-dimethoxy-5-methylhydroquinone renders the defensive secretion of Acladocricus setigerus (Silvestri, 1897) significantly different from that of other quinone-producing millipedes. In addition, two hitherto undescribed compounds, namely, 2,3-dimethoxy-5-methylhydroquinone and 2-methyl-3,4-methylenedioxyphenol, were characterized from the defensive secretion. However, it is uncertain if the latter compound is formed after the release of the secretion. The two major compounds, 2-methyl-1,4-benzoquinone and 2-methoxy-3-methyl-1,4-benzoquinone, constitute about 75% of the defensive fluid. Furthermore, hydrocarbons, which are typically present in the secretions of most other arthropods that use benzoquinones as repellents, are notably absent in the secretion of A. setigerus.

show abstract

“…5 Moreover, the ability to effect exclusive dehydrogenation in the presence of sensitive substituents such as alcohols and phenols (eq 2) 5b illustrates the mildness of the method and represents a further advantage. 40 It has been suggested that oxidation proceeds in this instance as a result of relief of steric strain. 1d,7 Skeletal rearrangements are relatively uncommon features of quinone-mediated dehydrogenation reactions, but 1,1-dimethyltetralin readily undergoes aromatization with a 1,2-methyl shift when subjected to the usual reaction conditions (eq 4).…”

Section: Introductionmentioning

confidence: 97%

“…DDQ is a particularly effective aromatization reagent and is frequently the reagent of choice to effect facile dehydrogenation of both simple (eq 3) 6 and complex hydroaromatic carbocyclic compounds. 40 Allylic and benzylic alcohols, on the other hand, are readily oxidized to the corresponding carbonyl compounds, 1b, 41 and procedures have been developed which utilize catalytic amounts of the reagent in the presence of a stoichiometric amount of a second oxidant. 8 Wagner-Meerwein rearrangements have also been observed in the aromatization of steroids (eq 5), although in this instance considerably longer reaction times are required.…”

Section: Introductionmentioning

confidence: 99%

2,3-Dichloro-5,6-dicyano-1,4-benzo-quinone

Buckle¹,

Collier²,

McLaws³

2005

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

The stereospecific oxidation of saturated secondary alcohol with dichlorodicyanoquinone

Cited by 18 publications

References 5 publications

Voltammetric Determination of Pb, Cu and Hg in Biodiesel Using Gold Screen‐printed Electrode: Comparison of Batch‐injection Analysis with Conventional Electrochemical Systems

Voltammetric Determination of Pb, Cu and Hg in Biodiesel Using Gold Screen‐printed Electrode: Comparison of Batch‐injection Analysis with Conventional Electrochemical Systems

Hydroquinones from defensive secretion of a giant Pacific millipede, Acladocricus setigerus (Diplopoda: Spirobolida)

2,3-Dichloro-5,6-dicyano-1,4-benzo-quinone

Contact Info

Product

Resources

About