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Titolo:
FACIAL SELECTIVITY IN CYCLOADDITIONS OF A CHIRAL KETENE ACETAL UNDER MICROWAVE IRRADIATION IN SOLVENT-FREE CONDITIONS - CONFIGURATIONAL ASSIGNMENT OF THE CYCLOADDUCTS BY NOESY EXPERIMENTS AND MOLECULAR MECHANICS CALCULATIONS
Autore:
DIAZORTIZ A; DIEZBARRA E; DELAHOZ A; PRIETO P; MORENO A; LANGA F; PRANGE T; NEUMAN A;
Indirizzi:
UNIV CASTILLA LA MANCHA,FAC QUIM E-13071 CIUDAD REAL SPAIN UNIV CASTILLA LA MANCHA,FAC QUIM,SECC TOLEDO E-45001 TOLEDO SPAIN CNRS,URA 1430 F-93012 BOBIGNY FRANCE
Titolo Testata:
Journal of organic chemistry
fascicolo: 13, volume: 60, anno: 1995,
pagine: 4160 - 4166
SICI:
0022-3263(1995)60:13<4160:FSICOA>2.0.ZU;2-1
Fonte:
ISI
Lingua:
ENG
Soggetto:
DIELS-ALDER REACTION; REARRANGEMENT;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
36
Recensione:
Indirizzi per estratti:
Citazione:
A. Diazortiz et al., "FACIAL SELECTIVITY IN CYCLOADDITIONS OF A CHIRAL KETENE ACETAL UNDER MICROWAVE IRRADIATION IN SOLVENT-FREE CONDITIONS - CONFIGURATIONAL ASSIGNMENT OF THE CYCLOADDUCTS BY NOESY EXPERIMENTS AND MOLECULAR MECHANICS CALCULATIONS", Journal of organic chemistry, 60(13), 1995, pp. 4160-4166

Abstract

(R)-4-Phenyl-2-methylene-1,3-dioxolane (1) undergoes 1,3-dipolar and Diels-Alder cycloadditions under microwave irradiation within 3 min with excellent yields, a simple purification procedure, and an interesting facial selectivity. The stereochemistry of these cycloadducts has been inferred by NOESY experiments and molecular mechanics calculations. X-ray structure determination was required in one case. Thermal isomerization of the cycloadducts was performed affecting only the spiro-carbon. The Diels-Alder adducts in the presence of a slight amount of acid yield the corresponding open chain esters.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/12/20 alle ore 10:35:04