Ueber Dicarboxylglutarsäureester

Guthzeit, M.; Dressel, O.

doi:10.1002/cber.18880210212

Cited by 10 publications

(2 citation statements)

References 2 publications

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“…The reaction of diethyl malonate (1) and diiodomethane in the presence of sodium ethoxide was first reported by Guthzeit and Dressel in 1888. 3,4 They used a half equivalent of diiodomethane and obtained 84% of tetraethyl 1,1,3,3-propanetetracarboxylate (2).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of trialkyl 2-halogeno-1,1,1-ethanetricarboxylates

Zinczuk¹,

Carnavale²

2016

Arkivoc

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A series of trialkyl 2-halogeno-1,1,1-ethanetricarboxylates (Hal = Cl, Br, I) was obtained in high yields by halomethylenation of trialkyl methanetricarboxylates that in turn were derived from dialkyl malonates. The variables that control the reaction (solvent, temperature, time of reaction, base, and alkylating agent) were adjusted to optimize the yield. This new family of compounds may be considered as synthetic equivalents of the unstable dialkyl (halomethyl)malonates.

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Section: Introductionmentioning

confidence: 99%

“…5 In turn, F. Tutin carried out the reaction under identical conditions but obtained only 20% of product. 6 Using diiodomethane in place of dichloromethane he obtained a mixture of unreacted 1 and diethy methylenemalonate (3). The expected 2 was not detected.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of trialkyl 2-halogeno-1,1,1-ethanetricarboxylates

Zinczuk¹,

Carnavale²

2016

Arkivoc

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The Alkylation of Esters and Nitriles

2011

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This chapter is concerned with the reactions of metal salts (enolates) of active methylene compounds with alkylating agents such as alkyl halides to produce allyl derivatives. The first example of this reaction is found in the literature when Geuther prepared ethyl alpha‐ethyl acetoacetate by the reaction of the sodium enolate of ethyl acetoacetate with ethyl iodide. The active methylene compounds considered in the chapter include malonic esters, cyanoacetic esters, malonitriles, monocarboxylic esters and mononitriles. These classes of compounds are characterized by the presence of one or more acidic hydrogen atoms attached to carbon. Only C‐alkylation has been observed with active methylene compounds and are discussed here. Several alternative methods for the preparation of alkyl and aryl derivatives of carboxylic esters and nitriles have been included.

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Verein deutscher Chemiker

1935

Angewandte Chemie

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Ueber Dicarboxylglutarsäureester

Cited by 10 publications

References 2 publications

Synthesis of trialkyl 2-halogeno-1,1,1-ethanetricarboxylates

Synthesis of trialkyl 2-halogeno-1,1,1-ethanetricarboxylates

The Alkylation of Esters and Nitriles

Verein deutscher Chemiker

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