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Titolo:
Reaction of alkyl and aryl grignard reagents with trifluoroacetyldihydropyrans and other cyclic beta-alkoxy-alpha,beta-unsaturated trifluoromethylketones
Autore:
Mellor, JM; Reid, G; El-Sagheer, AH; El-Tamany, ESH;
Indirizzi:
Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England Univ Southampton Southampton Hants England SO17 1BJ 7 1BJ, Hants, England Suez Canal Univ, Fac Sci, Dept Chem, Ismalia, Egypt Suez Canal Univ Ismalia Egypt Univ, Fac Sci, Dept Chem, Ismalia, Egypt
Titolo Testata:
TETRAHEDRON
fascicolo: 51, volume: 56, anno: 2000,
pagine: 10039 - 10055
SICI:
0040-4020(200012)56:51<10039:ROAAAG>2.0.ZU;2-3
Fonte:
ISI
Lingua:
ENG
Soggetto:
HUMAN-LEUKOCYTE ELASTASE; BENZYL COPPER REAGENTS; BETA-HYDROXY KETONES; TISHCHENKO REACTIONS; NONPEPTIDIC INHIBITORS; ANTENNAL ESTERASES; CARBONYL-COMPOUNDS; MEDIATED ADDITION; IN-VITRO; REDUCTION;
Keywords:
additions; A-strain; Grignard reagents; hydride transfer; tetrahydropyrans; trifluoromethylketones;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
66
Recensione:
Indirizzi per estratti:
Indirizzo: Mellor, JM Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England Univ Southampton Southampton Hants England SO17 1BJ s, England
Citazione:
J.M. Mellor et al., "Reaction of alkyl and aryl grignard reagents with trifluoroacetyldihydropyrans and other cyclic beta-alkoxy-alpha,beta-unsaturated trifluoromethylketones", TETRAHEDRON, 56(51), 2000, pp. 10039-10055

Abstract

Alkyl and aryl Grignard reagents react with cyclic beta -alkoxy-alpha,beta-unsaturated trifluoromethylketones by 1,il-addition to give as the major products, for example, cis-2,3-disubstituted tetrahydropyrans. In most examples ring opening leads to stereoselective formation of rearranged hemiketals as minor products. Under other conditions with 2,2,2-trifIuoro-1-(2-ethoxy-3,4-dihydro-2H-5-pyranyl)-1-ethanone stereoselective ring opening leads to acyclic aldehydes, as minor products and, by the major pathway, to a series of diols by addition of further equivalents of the Grignard reagent. Tnthe absence of further Grignard reagent at higher temperatures internal hydride transfer can afford acyclic esters. (C) 2000 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 21/09/20 alle ore 12:58:03