A Safer Diazotransfer Reagent

Hazen, George G.; Weinstock, Leonard M.; CONNELL, R.; Bollinger, F. W.

doi:10.1080/00397918108065754

Cited by 64 publications

(39 citation statements)

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“…The second reason is the additional safety aspect compared to most other diazo transfer reagents. DBSA is an oil at room temperature with an approximate initiation temperature of 151°C and an impact sensitivity of 150 kg⋅cm, compared to tosyl azide, which has an impact sensitivity of 50 kg⋅cm and an initiation temperature of 120°C [38].…”

Section: Resultsmentioning

confidence: 99%

Delivering Enhanced Efficiency in the Synthesis of α-Diazosulfoxides by Exploiting the Process Control Enabled in Flow

McCaw¹,

Deadman²,

Maguire³

et al. 2016

J Flow Chem

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Continuous-flow generation of α-diazosulfoxides results in a two-to three-fold increase in yields and decreased reaction times compared to standard batch synthesis methods. These high yielding reactions are enabled by flowing through a bed of polystyrene-supported base (PS-DBU or PS-NMe 2 ) with highly controlled residence times. This engineered solution allows the α-diazosulfoxides to be rapidly synthesized while limiting exposure of the products to basic reaction conditions, which have been found to cause rapid decomposition. In addition to improved yields, this work has the added advantage of ease of processing, increased safety profile, and scale-up potential.

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Section: Resultsmentioning

confidence: 99%

Delivering Enhanced Efficiency in the Synthesis of α-Diazosulfoxides by Exploiting the Process Control Enabled in Flow

McCaw¹,

Deadman²,

Maguire³

et al. 2016

J Flow Chem

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“…Further purification was achieved by distillation. 10,11 : To a solution of ethyl 4-methyl-3-oxo-pent-4-enoate in acetonitirile were added triethylamine and p-toluenesulfonyl azide at 0 o C. The mixture was stirred at 0 o C for 20 min and 25 o C for 2 h. The mixture was concentrated under reduced pressure and the residue was precipitated into the carbon tetrachloride. The precipitated p-toluene sulfonamide was removed by filtration.…”

Section: Preparation Of Monomersmentioning

confidence: 99%

Synthesis of copolymers containing diazoketo groups and their application as DUV resists

Kim

2005

SPIE Proceedings

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We synthesized a new type of polymers that have diazoketo groups instead of acid-labile protecting groups. The polymers do not need a photoacid generator for formulation of resists. That is, the new matrix polymers absorb UV light and produce carboxylic groups. Also, there is no necessity for a post-exposure bake step, which is the cause of postexposure delay effects. New monomer, ethyl 2-diazo-4-methyl-3-oxo-pent-4-enoate was synthesized. This monomer was copolymerized with hydroxystyrene and adamantyl methacrylate. After UV exposure, the polymers became soluble in an aqueous base developer. The polymers showed bleaching effect after UV exposure. Thermal properties of the polymers were measured by TGA and DSC. Characterization of the polymers has been done using other techniques such as FT-IR, NMR, GPC, and UV. The resist patterns of 0.8 µm feature size were resolved using a DUV contact printer and with a tetramethylammonium hydroxide aqueous solution.

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“…, T Zers. , Schlagempfindlichkeit) lassen sich die Vorteile von p-Dodecylbenzolsulfonylazid [23] (Gemisch von Stellungsisomeren) erkennen, dessen Sulfonamid darüber hinaus flüssig ist und somit auch Vorteile bei der Abtrennung von kristallinen Diazoverbindungen bietet. Dennoch scheint dieses Reagens bisher kaum Eingang in die Laborpraxis gefunden zu haben.…”

Section: Diazogruppenübertragung Auf Aktivierte Methylenverbindungenunclassified

Neues zur Synthese von Diazoverbindungen

Maas

2009

Angewandte Chemie

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Aufgrund der vielseitigen und nützlichen Folgechemie von Diazoverbindungen (R1R2CN2) ist das Interesse an dieser Substanzklasse seit Jahren ungebrochen. Dabei wird auch das bereits vorhandene Methodenrepertoire zur Herstellung von Diazoverbindungen immer wieder um neue Verfahren oder um neuartige Varianten etablierter Synthesewege ergänzt. Nicht selten tragen die neuen Synthesevorschläge der Labilität und beachtlichen chemischen Reaktivität bestimmter Typen von Diazoverbindungen Rechnung, aber auch dem Aspekt umweltfreundlicherer Methodik wurde Beachtung geschenkt.

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A Safer Diazotransfer Reagent

Cited by 64 publications

References 1 publication

Delivering Enhanced Efficiency in the Synthesis of α-Diazosulfoxides by Exploiting the Process Control Enabled in Flow

Delivering Enhanced Efficiency in the Synthesis of α-Diazosulfoxides by Exploiting the Process Control Enabled in Flow

Synthesis of copolymers containing diazoketo groups and their application as DUV resists

Neues zur Synthese von Diazoverbindungen

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