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Titolo:
Unusual head-to-tail coupling of alkyl benzoates by electroreduction
Autore:
Kise, N; Hirata, Y; Ueda, N;
Indirizzi:
Tottori Univ, Fac Engn, Dept Biotechnol, Tottori 6808552, Japan Tottori Univ Tottori Japan 6808552 pt Biotechnol, Tottori 6808552, Japan
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 3, volume: 66, anno: 2001,
pagine: 862 - 867
SICI:
0022-3263(20010209)66:3<862:UHCOAB>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
O-METHYL OXIMES; ELECTROORGANIC CHEMISTRY; BETA-CYCLODEXTRIN; AROMATIC KETONES; CONVENIENT ROUTE; ESTERS; 1,2-DIKETONES; ACETOPHENONE; DIMERIZATION; REDUCTION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
19
Recensione:
Indirizzi per estratti:
Indirizzo: Kise, N Tottori Univ, Fac Engn, Dept Biotechnol, Tottori 6808552, Japan Tottori Univ Tottori Japan 6808552 chnol, Tottori 6808552, Japan
Citazione:
N. Kise et al., "Unusual head-to-tail coupling of alkyl benzoates by electroreduction", J ORG CHEM, 66(3), 2001, pp. 862-867

Abstract

The electroreduction of alkyl benzoates in an alcoholic solvent gave unusual head-to-tail coupled products. Usual head-to-head coupled products derived from acyloin condensation could not be detected. The best result (73% yield) was obtained from methyl benzoate using an undivided cell with an Sn cathode in i-PrOH containing tetraalkylammonium salt sis a supporting electrolyte. Using an undivided cell, the products cross-coupled with a solvent molecule were obtained as byproducts. The substitution at the para position of methyl benzoate considerably decreased the yields of the head-to-tail coupled products and increased those of the cross-coupled products. The possible mechanism of the head-to-tail coupling is the attack of anion radical, generated from methyl benzoate by one-electron transfer, to another methyl benzoate. The cross-coupled products were formed by the reaction with carbonyl compound anodically produced from a solvent molecule. The cross-coupling between methyl benzoate and aromatic aldehydes was also effected by the mixed electroreduction under the same conditions.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/01/20 alle ore 16:13:35