The use of tetramethylguanidinium azide in non-halogenated solvents avoids potential explosion hazards

Li, C.; Shih, Tzenge‐Lien; Jeong, Jae Uk; Arasappan, Ashok; Fuchs, P. L.

doi:10.1016/s0040-4039(00)76995-4

Cited by 29 publications

(13 citation statements)

References 3 publications

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“…The Zhdankin reagent (a stable azidoiodinone) was used for the direct azidation of hydrocarbons (see Scheme ) 145. An important reagent is tetramethylguanidinium azide introduced by Papa212 which has been used for the synthesis of vinyl azides,69 among others (Section 3.2) and is advantageous for safety reasons 213…”

Section: Synthesis Of Organic Azidesmentioning

confidence: 99%

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

et al. 2005

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Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza-Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer-Aubé rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.

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Section: Synthesis Of Organic Azidesmentioning

confidence: 99%

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

et al. 2005

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“…Das Zhdankin‐Reagens (ein stabiles Azidoiodinon) wird zur direkten Azidierung von Kohlenwasserstoffen verwendet (siehe Schema ) 145. Ein wichtiges Reagens ist das von Papa212 eingeführte Tetramethylguanidiniumazid, das unter anderem zur Synthese von Vinylaziden69 eingesetzt wird (Abschnitt 3.2) und auch aus Sicherheitsgründen vorteilhaft ist 213…”

Section: Synthese Von Organischen Azidenunclassified

Organische Azide – explodierende Vielfalt bei einer einzigartigen Substanzklasse

et al. 2005

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Seit der Entdeckung der organischen Azide vor über einhundertvierzig Jahren durch Peter Grieß wurde eine Reihe von Synthesen für diese energiereichen Moleküle entwickelt. In letzter Zeit haben sich völlig neue Perspektiven durch Anwendungen in der Peptidchemie, der kombinatorischen Chemie und der Heterocyclensynthese ergeben. Auf dem interdisziplinären Gebiet zwischen Chemie, Biologie, Medizin und Materialwissenschaften nehmen organische Azide inzwischen einen wichtigen Raum ein. In diesem Aufsatz werden die Grundzüge der Azid‐Chemie dargelegt und aktuelle Entwicklungen auf diesem Gebiet beleuchtet. Der Schwerpunkt liegt dabei auf Cycloadditionen (Huisgen‐Reaktion), Aza‐Ylidchemie und der Synthese von Heterocyclen. Weitere Reaktionen wie die Aza‐Wittig‐Reaktion, Sundberg‐Umlagerung, Staudinger‐Ligation, Boyer‐ und Boyer‐Aubé‐Umlagerung, Curtius‐Umlagerung, Schmidt‐Umlagerung sowie die Hemetsberger‐Umlagerung zeugen von der Vielfältigkeit moderner Azid‐Chemie.

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“…TMGA (28) will convert to tetramethylguanidinium salt after completion of the azidation reaction, offering easy isolation of azide product from the reaction mixture by addition of diethyl ether. TMGA (28) is commercially available, nontoxic and safe to handle [107]. Thus, TMGA (28) participating azidation has been established as a widely applicable and simple operating method for the introduction of a nitrogen source in a variety of organic syntheses [108].…”

Section: Ionic Liquidmentioning

confidence: 99%

“…Glycosyl halides are reacted with 28 to afford the corresponding glycosyl azides in quantitative yields; complete inversion at the anomeric centre is observed in this reaction [107] (Scheme 4.43).…”

Section: Ionic Liquidmentioning

confidence: 99%

Guanidines in Organic Synthesis

Ishikawa

2009

Superbases for Organic Synthesis

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The use of tetramethylguanidinium azide in non-halogenated solvents avoids potential explosion hazards

Cited by 29 publications

References 3 publications

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Organische Azide – explodierende Vielfalt bei einer einzigartigen Substanzklasse

Guanidines in Organic Synthesis

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