Synthesen von β‐Carotin und Lycopin aus Octen‐(4)‐dion‐(2.7)

Kabbe, Hans‐Joachim; Truscheit, Ernst; Eiter, K.

doi:10.1002/jlac.19656840105

Cited by 9 publications

(1 citation statement)

References 11 publications

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“…185 These reactions are, in principle, also mediated by acids alone (e.g., formic acid), but in connection with the Ruppe rearrangement, where the enyne is initially formed by acid-mediated elimination from a propargyl alcohol (section 5.1.3). Nonconjugated a,w-dialkynes are hydrated to diketones, 186,187 see Scheme 11 for catalysis by gold(I). The hydration of a terminal alkyne in the presence of an internal alkyne was performed selectively with mercury(II) oxide-boron trifluoride-methanol, in cases where a mercury(II) sulfate catalyst gave mixtures of diketones.…”

Section: Terminal Alkynes Bearing Carbon Functionalitymentioning

confidence: 99%

Catalytic Hydration of Alkynes and Its Application in Synthesis

Hintermann¹,

Labonne²

2007

Synthesis

398

261

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The catalytic addition of water to alkynes (hydration) generates valuable carbonyl compounds from unsaturated hydrocarbon precursors. Traditional mercury(II) catalysts hydrate terminal alkynes with Markovnikov selectivity to methyl ketones. Much research has been devoted to finding catalysts based on less toxic metals, the most promising being gold(I), gold(III), platinum(II), and palladium(II). Catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been realized in an efficient manner with ruthenium(II) complex catalysts. The present review article lists known hydration catalysts and discusses applications of catalytic hydration to different classes of substrates, with an emphasis on functional group tolerance and regioselectivity. 6 Reactions Related to Catalytic Alkyne Hydration 7 Conclusions and Outlook

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Section: Terminal Alkynes Bearing Carbon Functionalitymentioning

confidence: 99%