Portal de Periódicos da CAPES

Artigo Produção Nacional Revisado por pares

BIBTEX RIS

Hydroalumination of Thioacetylenes: A Versatile Generation and Reactions of α-Aluminate Sulfides Intermediates

2008; Taylor & Francis; Volume: 38; Issue: 24 Linguagem: Inglês

10.1080/00397910802369497

1532-2432

Palimécio G. Guerrero, Miguel J. Dabdoub, F. A. Marques, Celso L. Wosch, Adriano C. M. Baroni, Antônio G. Ferreira,

Synthesis of heterocyclic compounds

Abstract Hydroalumination of thioacetylenes using DIBAL-H and lithium di-(isobutyl)-n-(butyl)-aluminate hydride (Zweifel's reagent), followed by addition of water, furnished exclusively the (Z)- and ( E )-vinyl sulfides, respectively. The regio- and stereochemistry of the intermediates generated, (Z)- and ( E )-phenylthio vinyl alanates, were determined by capture with iodine, which afforded the corresponding ( E )- and (Z)-1-iodo-1-phenylthio-2-organoyl ethenes. Reactions of the ( E )-iodo(thio)ketene acetals with n-BuLi followed by addition of hexanal afforded the (Z)-phenylthio allylic alcohol, while the (Z)-iodo(thio)ketene acetals under similar reactions conditions gave the ( E )-phenylthio allylic alcohol exclusively.