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Titolo:
Synthesis, structures, and reactions of nitrogen, oxygen, and sulfur-functionalized silyl anions
Autore:
Kawachi, A; Tamao, K;
Indirizzi:
Kyoto Univ, Inst Chem Res, Uji 6110011, Japan Kyoto Univ Uji Japan 6110011 oto Univ, Inst Chem Res, Uji 6110011, Japan
Titolo Testata:
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
fascicolo: 9, volume: 59, anno: 2001,
pagine: 892 - 903
SICI:
0037-9980(200109)59:9<892:SSARON>2.0.ZU;2-R
Fonte:
ISI
Lingua:
JPN
Soggetto:
DOUBLE-BOND; WITTIG REARRANGEMENT; NORMAL-BUTYLLITHIUM; ARYL CYCLOPROPANES; ORGANIC-SYNTHESIS; TIN DERIVATIVES; LITHIUM; LITHIATION; CARBON; SUBSTITUTION;
Keywords:
silyl anion; silyllithium; silylenoid; silylene; tin-lithium exchange reaction; reductive lithiation; sila-Wittig rearrangement; cyclopropanation reaction; chirality transfer; hydroxy anion equivalent;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
90
Recensione:
Indirizzi per estratti:
Indirizzo: Tamao, K Kyoto Univ, Inst Chem Res, Uji 6110011, Japan Kyoto Univ Uji Japan 6110011 Inst Chem Res, Uji 6110011, Japan
Citazione:
A. Kawachi e K. Tamao, "Synthesis, structures, and reactions of nitrogen, oxygen, and sulfur-functionalized silyl anions", J SYN ORG J, 59(9), 2001, pp. 892-903

Abstract

Several types of nitrogen-, oxygen-, and sulfur-functionalized silyllithiums have been prepared as the first members of stable and/or well-characterizable functionalized silyl anions. These functionalized silyllithiums can be obtained mainly by tin-lithium exchange reaction of the corresponding silylstannanes with butyllithium and/or by reaction of the corresponding chlorosilanes with lithium. Described herein are also the general aspects of (1)high stability of [(amino) silyl]lithiums, (2) low stability of [(alkoxy)silyl]lithiums, behaving as silylenoid species, (3) low stability of [(arylthio)silyl]lithiums, affording silylenes, (4) structure analyses of the [(amino) silyl]lithiums in solution and in the solid state, (5) [2,3]-sila-Wittig rearrangement and cyclopropanation reaction of [(allyloxy)silyl]lithiumsand the chirality transfer during these reactions, (6) functionalized oligosilane synthesis using [ (amino) silyl] lithiums, and (7) synthetic application of (aminosilyl) lithiums as a hydroxy anion equivalent by a combination with the oxidative cleavage of the Si-C bonds.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 31/03/20 alle ore 22:25:09