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Titolo:
ADDITION OF AZOLES AND AMINES TO UNSYMMETRICAL FUMARIC ESTERS
Autore:
ZADERENKO P; LOPEZ MC; BALLESTEROS P;
Indirizzi:
UNED,FAC CIENCIAS,DEPT QUIM ORGAN & BIOL,C SENDA REY S-N MADRID SPAIN UNED,FAC CIENCIAS,DEPT QUIM ORGAN & BIOL MADRID SPAIN UNIV CASTILLA LA MANCHA,EU POLITECN ALMADEN,DEPT QUIM INORGAN ORGAN &BIOQUIM ALMADEN CIUDAD REAL SPAIN
Titolo Testata:
Journal of organic chemistry
fascicolo: 20, volume: 61, anno: 1996,
pagine: 6825 - 6828
SICI:
0022-3263(1996)61:20<6825:AOAAAT>2.0.ZU;2-O
Fonte:
ISI
Lingua:
ENG
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
14
Recensione:
Indirizzi per estratti:
Citazione:
P. Zaderenko et al., "ADDITION OF AZOLES AND AMINES TO UNSYMMETRICAL FUMARIC ESTERS", Journal of organic chemistry, 61(20), 1996, pp. 6825-6828

Abstract

The regioselectivity of nucleophilic addition of azoles to unsymmetrical fumarates yielding the corresponding (+/-)-2-azol-1-ylsuccinates has been studied, The major regioisomer has been identified as the one obtained from the attack of the azole to the more congestive side of the double bond. These results have been interpreted in terms of HOMO-LUMO interactions using semiempirical AM1 molecular orbital calculations, Addition of amines as alternative heteronucleophiles has been also explored to confirm the regioselectivity. Neutral hydrolysis of the two n-butyl ethyl (+/-)-2-imidazol-1-ylsuccinate regioisomers 8a and 8b has shown that this hydrolysis takes place faster than with the corresponding symmetrical di-n-butyl (+/-)-2-imidazol-1-ylsuccinate, and theapparent rate of hydrolysis is independent of the size of the alcoholmoiety.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 07/07/20 alle ore 22:09:25