57592-45-7

Upstream product

• 64-67-5 diethyl sulfate 
• 74-96-4 ethyl bromide 
• 17455-13-9 18-crown-6 ether 
• 66279-50-3 acetoacetic acid ethyl ester; potassium (Z)-enolate 
• 23978-09-8 [2.2.2]cryptande 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 

Downstream Products

• 24704-57-2 methyl acetate-d₃ 
• 141-78-6 ethyl acetate 
• 141890-73-5 ethyl 3-(4-nitroanilino)-2-butenoate 
• 64334-94-7 ethyl 3-(3-nitroanilino)-2-butenoate 
• 63197-51-3 3-Ethoxy-5-phenyl-2,4-hexadiensaeure 
• 59721-35-6 (e)-4-(3-chloro-4-cyclohexyl-phenyl)-3-pentene-2-one 
• 684215-21-2 7-(2,4-dichlorophenyl)-2,6-dimethylpyrrolo[1,2-b]pyridazin-4-ol 
• 775345-70-5 7-(2-chloro-4-methoxyphenyl)-2,6-dimethylpyrrolo[1,2-b]pyridazin-4-ol 
• 408308-16-7 4-ethoxy-6-cyclopent-1-enyl-5,6-dihydro-pyran-2-one 
• 100972-22-3 (+/-)-3-ethoxy-5-phenyl-hex-2c-enoic acid 
• 90968-38-0 1-benzyl-4-ethoxy-Δ³-pyrrolin-2-one 
• 90968-46-0 1-Benzyl-3-ethoxypyrrole 
• 90968-42-6 1-Methyl-3-ethoxypyrrole 
• 5435-93-8 4-ethoxy-6-phenyl-5,6-dihydropyran-2-one 

Relevant academic research and scientific papers

EFFET DE SOLVANT SUR SUPPORT SOLIDE: COMPARAISON DE POLYMERES PORTEURS DE MOTIFS HEXAMETHYLPHOSPHOROTRIAMIDE, N-PYRROLIDONE ET N-OXAZOLIDINONE SUR L'ALKYLATION DE L'ENOLATE DE L'ACETYLACETATE D'ETHYLE

The rate of ethylation by Et2SO4 of potassium enolate of ethylacetoacetate is enhanced in the presence of polymers bearing N-pyrrolidone (P-N.P.) or N-oxazolidone (P-N.O.) moieties.It depends inter alia on the nature of the polymeric skeleton.The C/O alkylation as well as the ratio E/Z of the enol ethers gives an account of the interaction of the enolate with its associated cation inside the polymer: the efficiency is thus: P-HMPA > P-N.P. > P-N.O., although a different order is observed on the reaction rate: P-HMPA > P-N.O. > P-N.P..Thus, this test reaction gives more information on the different interactions involved than the study of rate enhancements of nucleophilic substitutions.

INFLUENCE DE LA SOLVATATION PAR LE TERT-BUTANOL SUR LA STRUCTURE ET LA REACTIVE DE L'ENOLATE DE POTASSIUM DE L'ACETYLACETATE D'ETHYLE EN PRESENCE DE COURONNE OU DE CRYPTAND. ETUDE PAR SPECTROMETRIE INFRA-ROUGE ET CINETIQE.

The structure and the nucleophilic reactivity of crowned (18-crown-6) or crypted potassium ethyl acetoacetate enolate have been compared in tert-butanol and in DME (or THF).In the protic solvent tert-butanol, the crowned and the cryptated potassium enolate species both exist as loose ion pairs in which the enolate anion, strongly hidrogen-bonded to the solvent, is in a "transoid" (non chelating) conformation.Both species show similar reactivities towards alkylating agents but completely different reactivities are observed in aprotic weakly dissociating media (THF, DME).In contrast to what is observed in tert-bu tanol, the cryptated species and the crowned species have very different nucleophilic reactivities in THF or DME: in those solvents only the cryptated species retains a loose ion pair structure; the crowned species is a contact ion pair in which the enolate anion chelates the potassium cation.The solvatation of this crowned chelate species by tert-butanol has been demonstrated in binary mixtures of solvents (C6D6-t-BuOH, THF-t-BuOH).The oxygen basicity of the enolate anion is very different in the crowned chelated ion pair compared with the cryptand separated ion pair.