Hydroalumination and related reactions of phenyl 1-(trimethylsilyl)propadienyl sulfide followed by quenching with carbonyl compounds

Junji Tanaka, S. Kanemasa, O. Tsuge

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Abstract

Phenyl 1-(trimethylsilyl)propadienyl sulfide undergoes a hydroalumination with diisobutylaluminum hydride (DIBAH) or lithium butyl(diisobutyl)aluminum hydride (BL-DIBAH). The adduct anion derived from DIBAH is regioselectively trapped with carbonyl compounds at the position α to the phenylthio moiety to give 1,3-dienes as Peterson olefination products; the anion derived from BL-DIBAH is trapped at the position γ to the phenylthio moiety to give 3-buten-1-ols. Silylmetalation and stanylalumination on the same acceptor have been also briefly investigated as equivalent reactions.

Original languageEnglish
Pages (from-to)51-56
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume63
Issue number1
DOIs
Publication statusPublished - Jun 22 1990

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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