Nouvelle synthese de dialkyl-1,2 acetylcyclopropenes

Vidal, Michel; Chollet, Eliane; Arnaud, Paul

doi:10.1016/s0040-4039(00)90639-7

Cited by 11 publications

(3 citation statements)

References 5 publications

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“…First, we have synthesized a series of substituted [1,1′-bi(cyclopropan)]-2′-en-1-ols 1a–h from the corresponding substituted ethyl cycloprop-2-ene-1-carboxylates by Kulinkovich cyclopropanation (Scheme ). , The starting material ethyl cycloprop-2-ene-1-carboxylates could be easily prepared by Rh(II)-catalyzed cyclopropanation of alkyne with ethyl diazoacetate. , The cyclopropanols 1a–h were then converted to the corresponding silyl ethers 3 ( vide infra ). The overall yields for two steps ranged from 27% to 65%.…”

Section: Resultsmentioning

confidence: 99%

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Zn(II)- or Rh(I)-Catalyzed Rearrangement of Silylated [1,1′-Bi(cyclopropan)]-2′-en-1-ols

Zhang

Xie

et al. 2014

J. Org. Chem.

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The rearrangement reactions of silylated alcohols bearing the highly strained structures of cyclopropene and cyclopropanol connected in adjacent positions have been studied under ZnI2- and Rh(I)-catalyzed conditions. The results show intriguing carbon skeletal reorganizations of such system under these conditions. The ZnI2-catalyzed reaction proceeds with C-O cleavage and the rearrangement of the resultant carbon cation, leading to the breaking of the C-C single bond that connects two three-memebered rings. In contrast, the Rh(I)-catalyzed reaction involves σ-bond oxidative addition of the cyclopropene moiety, followed by β-carbon elimination of the cyclopropane moiety.

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Section: Resultsmentioning

confidence: 99%

“…The corresponding cyclopropene esters for the preparation of 1a , 1b , 1c , 1e , 1f , 1g , and 1h were known and were prepared via literature procedures. , The cyclopropene ester for preparing 1d is synthesized by the following procedure.…”

Section: Methodsmentioning

confidence: 99%

Zn(II)- or Rh(I)-Catalyzed Rearrangement of Silylated [1,1′-Bi(cyclopropan)]-2′-en-1-ols

Zhang

Xie

et al. 2014

J. Org. Chem.

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“…Experimental 1,2-Diethylcyclopropene-3-carboxylic acid was prepared from 3-hexyne with ethyl diazoacetate. [4] 2-Hydroxyethyl ester of the cyclopropene derivative as pendant moiety of polymer was prepared from its acid chloride.…”

Section: Introductionmentioning

confidence: 99%

Aromatization of Cyclopropene Dimer in Non-aromatic Photopolymer.

Miyagawa

Nakayama

Takahara

et al. 1999

J. Photopol. Sci. Technol.

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Preparation of Ketones from the Reaction of Organolithium Reagents with Carboxylic Acids

Jorgenson

2011

Organic Reactions

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The reaction of organolithium reagents and carboxylic acids constitutes a simple general method for the synthesis of ketones. This preparative route is the method of choice for direct conversion of carboxylic acid to ketones. It is the purpose of this chapter to evaluate critically the scope and limitations of this reaction and to recommend optimal conditions for its applications. The reaction of organolithium reagents with carboxylic acid is limited to the preparation of acyclic ketones. Although the objective of this reaction, the formation of unsymmetrical ketones, the method is clearly applicable to the synthesis of symmetrical ketones. Two different routes are possible and are discussed. To date, the reaction has been applied only to the preparation of monoketones.

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Nouvelle synthese de dialkyl-1,2 acetylcyclopropenes

Cited by 11 publications

References 5 publications

Zn(II)- or Rh(I)-Catalyzed Rearrangement of Silylated [1,1′-Bi(cyclopropan)]-2′-en-1-ols

Zn(II)- or Rh(I)-Catalyzed Rearrangement of Silylated [1,1′-Bi(cyclopropan)]-2′-en-1-ols

Aromatization of Cyclopropene Dimer in Non-aromatic Photopolymer.

Preparation of Ketones from the Reaction of Organolithium Reagents with Carboxylic Acids

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