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Titolo:
Selective electrochemical oxidation of heteroatom compounds having both silicon and tin on the same carbon as electroauxiliaries
Autore:
Yoshida, J; Watanabe, M; Toshioka, H; Imagawa, M; Suga, S;
Indirizzi:
Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 Biol Chem, Sakyo Ku, Kyoto 6068501, Japan
Titolo Testata:
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
fascicolo: 1-2, volume: 507, anno: 2001,
pagine: 55 - 65
Fonte:
ISI
Lingua:
ENG
Soggetto:
NONSTABILIZED AZOMETHINE YLIDES; ONE-ELECTRON OXIDATION; SEQUENTIAL DOUBLE DESILYLATION; BOND-CLEAVAGE REACTIONS; ALPHA-STANNYL ETHERS; ANODIC-OXIDATION; CATION RADICALS; ORGANOSILICON COMPOUNDS; CYCLIZATION REACTIONS; 3+2 CYCLOADDITION;
Keywords:
electrosynthesis; rotating disk electrode; anodic oxidation; electroauxiliary;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
70
Recensione:
Indirizzi per estratti:
Indirizzo: Yoshida, J Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, SakyoKu, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 Sakyo Ku, Kyoto 6068501, Japan
Citazione:
J. Yoshida et al., "Selective electrochemical oxidation of heteroatom compounds having both silicon and tin on the same carbon as electroauxiliaries", J ELEC CHEM, 507(1-2), 2001, pp. 55-65

Abstract

The selective electrochemical oxidation of heteroatom compounds having twodifferent electro auxiliaries, i.e. silicon and tin, on the same alpha -carbon was examined. The oxidation potentials of such compounds were found tobe similar to those of the corresponding compounds having only tin, indicating the predominant role of tin over that of silicon. The HOMO levels obtained by the molecular orbital calculations were consistent with the experimental results. The molecular orbital calculation of the cation radical suggests the selective cleavage of the C-Sn bond by the oxidation. Preparative electrochemical oxidation gave rise to selective cleavage of the C-Sn bond and the introduction of a nucleophile to the carbon. The C-Si bond was not affected at all. The product can also be further oxidized using the silyl group as an electro auxiliary. The second oxidation proceeded smoothly to cleave the C-Si bond and a second nucleophile was introduced on the same carbon. The present study indicates the feasibility of the redox potential based selective sequential transformation using electroauxiliaries. (C) 2001 Elsevier Science B.V. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 04/04/20 alle ore 11:50:59