A New and Selective Method of Oxidation. The Conversion of Alkyl Halides and Alkyl Tosylates to Aldehydes

Kornblum, Nathan; Jones, Willard J.; Anderson, George

doi:10.1021/ja01524a080

Cited by 396 publications

(128 citation statements)

References 2 publications

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“…Kornblum reaction is an oxidation of benzyl bromide to benzaldehyde by DMSO in basic aqueous conditions. [9][10][11] However, in the absence of both a base and water, Kornblum reaction cleanly afforded trimethylsulfonium bromide in excellent isolated yields (65-100%) depending on substituents in benzyl bromide. 6,12 In order to explain high quantitative yields of trimethylsulfonium bromide it was proposed that methyl bromide and dimethyl sulfide were produced not only from the reaction of Kornblum reaction (Scheme 1) but also from decomposition of DMSO itself.…”

Section: Resultsmentioning

confidence: 99%

Facile Preparation of Copper(I) Halide-Dimethyl Sulfide Complex and Its Application

2007

Bulletin of the Korean Chemical Society

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A preparative method of Me2SCuX (X = Cl, Br) via one-pot reaction was developed from common chemicals such as benzyl halide, DMSO, and Cu(0). In the reaction mixture small molecules such as methyl halide and dimethyl sulfide etc. were efficiently generated in situ, resulting in the formation of Me2SCuX. Oxidation of Cu(0) in reacting with both benzyl halide (starting material) and methyl halide (in situ generated product) to Cu(I) followed by complexing with dimethyl sulfide (in situ generated product) could explain the formation of Me2SCuX. In particular we found out that heterogeneous reaction of Me2SCuX and arenediazonium tetrafluoroborate in acetonitrile was so effective to afford corresponding bromoaromatics under mild conditions.

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Section: Resultsmentioning

confidence: 99%

Facile Preparation of Copper(I) Halide-Dimethyl Sulfide Complex and Its Application

2007

Bulletin of the Korean Chemical Society

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“…8 The system sodium iodide-DMSO-S02 also showed a color from iodine formation. Oxidation of alkali iodides by DMSO in liquid SO2 has never been reported before.…”

Section: S57mentioning

confidence: 96%

Inhibition of radical polymerization in liquid sulfur dioxide by alkali iodide and dimethylsulfoxide

Tokura

Kichiji

1962

J. Polym. Sci.

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“…The advantages of this model system are that AChE is a well-studied one-substrate enzyme and that preparation of the inhibitor solution for tacrine and bis(7)-tacrine does not require use of any co-solvent such as dimethyl sulfoxide, a mild oxidation reagent [20] that has an inhibitory effect on AChE [21].…”

Section: Cc-by 40 International License Peer-reviewed) Is the Authormentioning

confidence: 99%

On the use of the experimentally determined enzyme inhibition constant as a measure of absolute binding affinity

Darras

Pang

2017

Preprint

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Defined as a state function representing an inhibitor's absolute affinity for its target enzyme, the experimentally determined enzyme inhibition constant (K i ) is widely used to rank order binding affinities of different inhibitors for a common enzyme or different enzymes for a common inhibitor and to benchmark computational approaches to predicting binding affinity. Herein, we report that adsorption of bis (7)-tacrine to the glass container surface increased its K i against Electrophorus electricus acetylcholinesterase (eeAChE) to 3.2 ± 0.1 nM (n = 5) compared to 2.9 ± 0.4 pM (n = 5) that was determined using plastic containers with other assay conditions kept the same. We also report that, due to binding or "adsorption" of bis (7)-tacrine to the inactive eeAChE, the bis(7)-tacrine K i increased from 2.9 ± 0.4 pM (n = 5) to 734 ± 70 pM (n = 5) as the specific eeAChE activity decreased from 342 U/mg to 26 U/mg while other assay conditions were kept the same. These results caution against using K i s to rank order binding potencies, define selectivity, or benchmark computational methods without knowing detailed assay conditions.

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A New and Selective Method of Oxidation. The Conversion of Alkyl Halides and Alkyl Tosylates to Aldehydes

Cited by 396 publications

References 2 publications

Facile Preparation of Copper(I) Halide-Dimethyl Sulfide Complex and Its Application

Facile Preparation of Copper(I) Halide-Dimethyl Sulfide Complex and Its Application

Inhibition of radical polymerization in liquid sulfur dioxide by alkali iodide and dimethylsulfoxide

On the use of the experimentally determined enzyme inhibition constant as a measure of absolute binding affinity

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