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Titolo:
Synthesis and reactivity of conformationally locked alpha-aminoorganostannanes and alpha-aminoorganolithiums. Discovery of a surprising configurational requirement for transmetalation
Autore:
Chambournier, G; Gawley, RE;
Indirizzi:
Univ Miami, Dept Chem, Coral Gables, FL 33124 USA Univ Miami Coral GablesFL USA 33124 ept Chem, Coral Gables, FL 33124 USA
Titolo Testata:
ORGANIC LETTERS
fascicolo: 11, volume: 2, anno: 2000,
pagine: 1561 - 1564
SICI:
1523-7060(20000601)2:11<1561:SAROCL>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
SUBSTITUTION-REACTIONS; STEREOCHEMISTRY; EQUIVALENTS; DERIVATIVES; CARBANIONS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
18
Recensione:
Indirizzi per estratti:
Indirizzo: Gawley, RE Univ Miami, Dept Chem, POB 249118, Coral Gables, FL 33124 USA Univ Miami POB 249118 Coral Gables FL USA 33124 s, FL 33124 USA
Citazione:
G. Chambournier e R.E. Gawley, "Synthesis and reactivity of conformationally locked alpha-aminoorganostannanes and alpha-aminoorganolithiums. Discovery of a surprising configurational requirement for transmetalation", ORG LETT, 2(11), 2000, pp. 1561-1564

Abstract

[GRAPHICS]2-Tributylstannyl-N-methylpiperidines that are conformationally locked by a 4-tert-butyl substituent were evaluated in transmetalations (Sn-Li exchange) and reactions with electrophiles. When the tin is equatorial, transmetalation occurs smoothly as does reaction with carbonyl electrophiles. Alkyl halides seem to undergo single electron transfer reactions, affording nonselective alkylation products, along with products of radical disproportionation. In a surprise, an axially oriented tin failed to transmetalate, suggesting that a synclinal relationship between the nitrogen lone pair and the carbon-tin bond is a requirement for transmetalation.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 02/04/20 alle ore 18:44:21