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

DOI: 10.1246/bcsj.63.51

Source and publish data:

Bulletin of the Chemical Society of Japan p. 51 - 56 (1990)

Update date:2022-07-29

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Authors:

Tanaka Tanaka

Kanemasa

Tsuge Tsuge

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Article abstract of DOI:10.1246/bcsj.63.51

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.

Full text of DOI:10.1246/bcsj.63.51

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