Conversion of thioacetals to alkanes using Raney Nickel

by James

Description: Thioacetals can be desulfurized to give alkanes through the use of Raney nickel (“Ra-Ni”)
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Notes: This is an equivalent transforation to the Clemmensen and Wolff-Kishner reactions

Examples:

Notes: Note how in each case the thioacetal is converted into an alkane.

Mechanism: The method of action of Raney Nickel remains somewhat murky and for the purposes of Org 1/Org 2 the mechanism is not considered to be important. The hydrogen that replaces the sulfur is actually contained on the surface of the nickel.

Notes:

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{ 4 comments… read them below or add one }

naveen kumar

why the catalists are pyroporic in nature,while pure metals are not

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james

They’re pyrophoric because Raney Nickel has adsorbed hydrogen on it, as well as high surface area. So oxygen from the atmosphere will ignite the hydrogen, this leads to heat and spontaneous combustion.

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Stanton de Riel

Please correct: the “Alkylation of enamines” link also directs to this page.

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james

thank you!

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