[foxthreefour]

Does anyone know where I could find articles that have successfully carried out the reduction of an aromatic ketone to an alkane using Pd/C and hydrogen? I can't find references to an actual attempt or study.

[wildfyr]

Do you mean just the Ketone or the whole molecule, benzene ring and all?

[foxthreefour]

Just the ketone.

[rolnor]

A mixture of Pd/C and NaBH4 in methanol could work. Ketones are very resistant to hydrogenation, or? One could also convert the ketone to thioketone with Lawessonś reagent and desulphurize with Raney-Ni.

[phth]

A mixture of Pd/C and NaBH4 in methanol could work. Ketones are very resistant to hydrogenation, or? One could also convert the ketone to thioketone with Lawessonś reagent and desulphurize with Raney-Ni.

+1 this may be a good choice or conversion to a dithianeketal and Raney Ni reduction

[kriggy]

why dont make tosylhydrazon and decompose with KOH ? Wolf-Kishner reaction

[wildfyr]

I think you mean tolyl, tosyl is with a sulfonyl.

[sjb]

I think you mean tolyl, tosyl is with a sulfonyl.

I don't think it matters - the reactive bit is at the other end (the hydrazine)

[wildfyr]

Tosyl would mean you have the sulfonyl hydrazine as opposed to alkyl hydrazone, pretty different reactivity profiles.

[kriggy]

I think you mean tolyl, tosyl is with a sulfonyl.

yes I ment tosyl, it makes the NH more acidic. However, I recalled it wrong, the tosylhydrazone is then reduced with hydride and not with base, its called Caglioti reaction

Caglioti, L.; Magi, M. (1963). "The reaction of tosylhydrazones with lithium aluminium hydride". Tetrahedron. 19 (7): 1127

There are many different variants of K-W reaction, some of them even at room temperature

Furrow, M. E.; Myers, A. G. (2004). "Practical Procedures for the Preparation ofN-tert-Butyldimethylsilylhydrazones and Their Use in Modified Wolff−Kishner Reductions and in the Synthesis of Vinyl Halides andgem-Dihalides". Journal of the American Chemical Society. 126 (17): 5436–5445

Look up a wikipedia for mroe, their page on K-W reduction is pretty good