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Titolo:
Hydroalumination of phenylthioacetylenes. Synthesis and reactions of (Z)- and (E)-1-butyltelluro-1-phenylthio-1-alkenes
Autore:
Dabdoub, MJ; Guerrero, PG;
Indirizzi:
Univ Sao Paulo, Lab Sintese Compostos Organocalcogenios, Dept Quim, FFCLRP, BR-3900 Ribeirao Preto, SP, Brazil Univ Sao Paulo Ribeirao Preto SP Brazil BR-3900 ibeirao Preto, SP, Brazil
Titolo Testata:
TETRAHEDRON LETTERS
fascicolo: 41, volume: 42, anno: 2001,
pagine: 7167 - 7172
SICI:
0040-4039(20011008)42:41<7167:HOPSAR>2.0.ZU;2-C
Fonte:
ISI
Lingua:
ENG
Soggetto:
CROSS-COUPLING REACTIONS; ORGANOTELLURIUM COMPOUNDS; TELLURIUM EXCHANGE; PREPARATIVE METHOD; HYDROZIRCONATION; REAGENTS; TRANSFORMATION; ZINC;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
31
Recensione:
Indirizzi per estratti:
Indirizzo: Dabdoub, MJ Univ Sao Paulo, Lab Sintese Compostos Organocalcogenios, Dept Quim, FFCLRP, Av Bandeirantes, BR-3900 Ribeirao Preto, SP, Brazil Univ Sao Paulo Av Bandeirantes Ribeirao Preto SP Brazil BR-3900
Citazione:
M.J. Dabdoub e P.G. Guerrero, "Hydroalumination of phenylthioacetylenes. Synthesis and reactions of (Z)- and (E)-1-butyltelluro-1-phenylthio-1-alkenes", TETRAHEDR L, 42(41), 2001, pp. 7167-7172

Abstract

Hydroalumination of phenylthioacetylenes with the Zweifel's reagent as reducing agent followed by the addition of C4H9TeBr afforded (Z)-telluro(thio)ketene acetals (Z > 80-93%). The (E)-isomers were obtained with 100% stereoselectivity by reduction of thioacetylenes with DIBAL-H, followed by the addition of n-BuLi and subsequent treatment with C4H9TeBr. Reaction of the (E)-telluro(thio)ketene acetals with n-BuLi followed by the addition of valeraldehyde afforded the (Z)-phenylthio allylic alcohol as the main product and traces of the (E)-isomer. while the mixture of (Z)- and (E)-telluro(thio)ketene acetals under similar reaction conditions gave the (E)-phenylthio allylic alcohol exclusively. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 27/11/20 alle ore 02:07:02