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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
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- 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