The Intramolecular Radical Cation Induced Diels-Alder Reaction in the Diene - Diene Format

Rusterholz, David B.; Gorman, David B.; Gassman, Paul G.

doi:10.3390/20500080

Cited by 3 publications

References 20 publications

(38 reference statements)

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Corey‐Schmidt Oxidation

2010

Comprehensive Organic Name Reactions and Reagents

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The oxidation of organic compounds using pyridinium dichromate (PDC) is known as the PDC oxidation. PDC is a stable, bright orange solid and is less acidic than PCC but more acidic than the Collins reagent. In this reaction, primary alcohols can be oxidized to either aldehydes or carboxylic acids or even esters, depending on the substrate and solvent. The study finds that this oxidation has some advantages over other chromium‐based oxidations. It has been reported that when a methylamino group is present in the substrate alcohol, the oxidation using PDC does not succeed.

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Corey‐Schmidt Oxidation

2010

Comprehensive Organic Name Reactions and Reagents

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Reactivity Patterns of Radical Ions–A Unifying Picture of Radical‐Anion and Radical‐Cation Transformations

Schmittel¹,

Ghorai²

2001

Electron Transfer in Chemistry

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Thermal and Sonochemical Studies on the Diels−Alder Cycloadditions of Maskedo-Benzoquinones with Furans: New Insights into the Reaction Mechanism

et al. 2003

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What does a Diels-Alder cycloaddition look like? This question is here addressed in the case of the increasingly significant cycloadditions of masked o-benzoquinones (MOBs), which serve as versatile dienes for the construction of complex and functionalized structures. So first, what the mechanism is not: It is not (by and large) a classical, concerted [4 + 2] cycloaddition. Experimental evidence is now supported by sonochemical studies, which were instrumental in elucidating the pathway. Reactions with furans are accelerated and improved under sonication, even when conducted at -10 degrees C. Variation of the acoustic energy, temperature, and solvent composition allows us to optimize the yields and provide insights into the mechanism. Ultrasound does not cause sonochemical switching, as an alternative radical pathway should be ruled out. Results are consistent with a polar mechanism as claimed recently in a theoretical study. Moreover, this also does justice to a series of seminal papers, largely ignored, that gave a clue to the crucial issue of furan regioselectivity based on a nucleophilic addition. Most effects caused by ultrasonic agitation are of mechanochemical nature and suggest the existence of a perfectly stirred reactor with enhanced mass transfer.

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The Intramolecular Radical Cation Induced Diels-Alder Reaction in the Diene - Diene Format

Cited by 3 publications

References 20 publications

Corey‐Schmidt Oxidation

Corey‐Schmidt Oxidation

Reactivity Patterns of Radical Ions–A Unifying Picture of Radical‐Anion and Radical‐Cation Transformations

Thermal and Sonochemical Studies on the Diels−Alder Cycloadditions of Maskedo-Benzoquinones with Furans: New Insights into the Reaction Mechanism

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