Orthoameisensäureester als Alkylierungsmittel

Walther, Régis

doi:10.1002/prac.19150910113

Cited by 2 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Walther reported in 1915 that 2,4-dinitrophenol and 2,4,6-trinitrophenol are converted to the corresponding ethyl aryl ethers in high yield by heating them with triethyl orthoformate (289). Similarly, /?-nitrophenol is converted to ethyl /?-nitrophenyl ether in 67% yield by heating with triethyl orthoacetate (261).…”

Section: B Alkylation Of Phenolsmentioning

confidence: 99%

Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

1970

Carboxylic Ortho Acid Derivatives - Preparation and Synthetic Applications

View full text Add to dashboard Cite

In this chapter are considered reactions of trialkyl orthocarboxylates and tetraalkyl orthocarbonates which result in the formation of new carbonoxygen or carbon-halogen bonds. In most of these reactions the ortho ester (or an alkoxycarbonium ion derived from it) functions as an alkylating agent.Many of these reactions are useful synthetic tools. These include formation and hydrolysis of cyclic ortho ester derivatives of diols and triols (which serve to protect the hydroxyl groups of the polyols, and provide means for their mild monoacylation), alkylation of phenols, enols and acids (to form ethers and esters), and conversion of carbonyl compounds to acetals and ketals. Other reactions, such as the alkylation of halogens by ortho esters, are of only limited synthetic utility, while still others, such as the acidcatalyzed hydrolyses of ortho esters, are of interest primarily because of the light they shed on the mechanisms of reactions of ortho esters with nucleophilic reagents.

show abstract

Section: B Alkylation Of Phenolsmentioning

confidence: 99%

Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

1970

Carboxylic Ortho Acid Derivatives - Preparation and Synthetic Applications

View full text Add to dashboard Cite

show abstract

Über Gewinnung von Pikraten des Alkylpyridoniums und analoger Basen

Walther¹

1915

J. Prakt. Chem.

View full text Add to dashboard Cite

M e t h en yldiph enylhydrazidin a u s Formylphenylhydrazin und Anilin. Oeringe Mengen der Eomponenten wurden mit trockenem Benzol zu einem fliissigen Brei verriihrt und die doppelte Gewichtsmenge Phosphorsaureanhydrid in kleinen Portionen eingetragen, dann 1 Stunde lang auf dem Wasserbad erwarmt, wobei man das Benzol abdestillieren Ut, Die Masse wurde dann mit reichlich Wssser behandelt, von Ungelostem abfiltriert und dtls Filtrat mit Ammoniak nahezu neutralisiert; hierbei fie1 gin gelblicher, krystallinischer Niederschlag aus, der durch Umkrystallisieren aus Alkohol die Eydrazinbase in allerdings mangelhafter Ausbeute lieferte. Immerhin ist die Verbindung auf diesem Wege jederzeit zuganzlich, da Formylphenylhydrazin durch kurzes Aufkochen des Eydrazins mit 50prozent. Ameisensilure bekanntlich schnell zu erhalten ist.

show abstract

Orthoameisensäureester als Alkylierungsmittel

Cited by 2 publications

References 0 publications

Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

Über Gewinnung von Pikraten des Alkylpyridoniums und analoger Basen

Contact Info

Product

Resources

About