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Titolo:
Cathodically promoted stereoselective addition of 1,3-dinitro compounds tolevoglucosenone
Autore:
Niazimbetova, ZI; Evans, DH; Incarvito, CD; Rheingold, AL;
Indirizzi:
Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA Univ Delaware Newark DE USA 19716 pt Chem & Biochem, Newark, DE 19716 USA
Titolo Testata:
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
fascicolo: 5, volume: 147, anno: 2000,
pagine: 1868 - 1871
SICI:
0013-4651(200005)147:5<1868:CPSAO1>2.0.ZU;2-7
Fonte:
ISI
Lingua:
ENG
Soggetto:
CARBOHYDRATE FRAGMENT; HETEROCYCLIC-SYSTEMS; MICHAEL ADDITION; ETHYL NITROACETATE; NITROMETHANE; ALDEHYDES; ANION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Engineering, Computing & Technology
Citazioni:
20
Recensione:
Indirizzi per estratti:
Indirizzo: Niazimbetova, ZI Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA Univ Delaware Newark DE USA 19716 , Newark, DE 19716 USA
Citazione:
Z.I. Niazimbetova et al., "Cathodically promoted stereoselective addition of 1,3-dinitro compounds tolevoglucosenone", J ELCHEM SO, 147(5), 2000, pp. 1868-1871

Abstract

This paper reports new applications of the cathodically promoted addition of nitro compounds to the biomass-derived enone, levoglucosenone. A series of 2-substituted 1,3-dinitropropanes were found to undergo addition to levoglucosenone with generation of a tricyclic product containing a fused cyclohexane system. The reaction yields are good to excellent and are catalyzed by base (superoxide) generated electrochemically. Derivatives were preparedfrom 1,3-dinitropropane with the following. 2-substituents: 2-thienyl, 2-furyl, N-methyl-2-pyrryl, phenyl, 9-anthryl, and ferrocenyl. The structure of the derivative from 2-ferrocenyl-1,3-dinitropropane was established by X-ray crystallography, thus confirming the NMR-based stereochemical assignments of all of the other products. (C) 2000 The Electrochemical Society. S0013-4651(99)09-019-9. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/12/20 alle ore 12:32:16