New Examples of Electrolytic Methoxylation of Furans.

Nedenskov, Poul; Elming, Niels; Nielsen, Jørgen Tormod; Clauson-Kaas, Niels

doi:10.3891/acta.chem.scand.09-0017

Cited by 31 publications

(8 citation statements)

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“…16,17 The required furyl azide 8 was synthesized in a 53% yield by a Michael addition of sodium azide to 5-hydroxy-hex-3-yne-2-one (7) (Eq. 16,17 The required furyl azide 8 was synthesized in a 53% yield by a Michael addition of sodium azide to 5-hydroxy-hex-3-yne-2-one (7) (Eq.…”

Section: Resultsmentioning

confidence: 99%

A Thio-Staudinger Reaction: Thermolysis of a Vinyl Azide in the Presence of t -Butyl Mercaptan

Sauers

Arnum

2003

Phosphorus, Sulfur, and Silicon and the Related Elements

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The thermal decomposition of E-3-azido-3-hexene-2,5-dione (1) in protic media gave rise to several novel reactions of the azide 1 including adducts derived from keteneimine 11. Reaction with t-butyl mercaptan yielded two products, keteneimine-derived mercaptan addition product 20 and a sulfenimine 6. Trapping of a vinyl nitrene intermediate or a thio-Staudinger reaction was considered as a possible mechanism for the formation of sulfenimine 6. The absence of the vinyl nitrene addition products 3 and 5 when the thermal decomposition was conducted in either methanol or t-butylamine suggests a thio-Staudinger reaction is operative.

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Section: Resultsmentioning

confidence: 99%

A Thio-Staudinger Reaction: Thermolysis of a Vinyl Azide in the Presence of t -Butyl Mercaptan

Sauers

Arnum

2003

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…(entries 1, 2, [6][7][8][9][10][11][12][13][14] or furan rings incorporated in more complex structures (entries 15-18). The process is quite general regarding the degree of substitution on the furan ring but sensitive to the substituent nature.…”

Section: Methodsmentioning

confidence: 99%

Acid-Mediated Highly Regioselective Oxidation of Substituted Furans: A Simple and Direct Entry to Substituted Butenolides

Ceñal¹,

Carreras²,

Tonn³

et al. 2005

Synlett

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The scope and limitations of an expeditious synthesis of substituted butenolides from 3-substituted or 3,4-disubstituted furans is described. The entire process embodies a controlled oxidation of the furan core to a 2,5-dialkoxy-dihydrofuran intermediate and a regioselective acid-catalyzed hydrolysis to the butenolide derivative. 3-Substituted furans yield exclusively 2-substituted butenolides. Calculations studies provide substantiation of a proposed mechanism.

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“…[84][85][86] In 1955, Clauson-Kaas and co-workers described the dialkoxylation of various furans in an anodic oxidation protocol. 87,88 Electrolysis of the oxygen heterocycles on a platinum electrode in methanol and sulfuric acid or methanol and ammonium bromide electrolytes furnished a series of 2,5-dimethoxylated dihydrofuran products in good yields (Scheme 25). Although the authors included furylethanol as substrate for the electrooxidation, producing the hydroxy-decorated dimethoxydihydrofuran, they failed to perceive the opportunity to exploit the product in the title ring-expansion reaction.…”

Section: Anodic Oxidationsmentioning

confidence: 99%

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

2015

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Over the years, the oxidative ring enlargement of furfuryl alcohols, known as the Achmatowicz reaction, has been developed into a powerful and versatile synthetic tool for the preparation of 6-hydroxypyranones. This review provides a comprehensive collection of the various ways to perform Achmatowicz rearrangement reactions and explores the role of this ring-expansion process in contemporary organic synthesis. 1 Introduction 2 Classical Methods and Variants 3 Single-Electron-Transfer Oxidations 4 Metal-Catalyzed Ring Expansions 5 Photolytic Oxygenations 6 Enzymatic Transformations 7 Conclusions

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New Examples of Electrolytic Methoxylation of Furans.

Cited by 31 publications

References 0 publications

A Thio-Staudinger Reaction: Thermolysis of a Vinyl Azide in the Presence of t -Butyl Mercaptan

A Thio-Staudinger Reaction: Thermolysis of a Vinyl Azide in the Presence of t -Butyl Mercaptan

Acid-Mediated Highly Regioselective Oxidation of Substituted Furans: A Simple and Direct Entry to Substituted Butenolides

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

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