Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: xyzi on September 17, 2007, 12:43:35 AM
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hi!
I'm looking for the mechanism of hydrogenolysis of N-benzyl group using Pd on C, cyclohexene and methanol (as solvent) but I've gone as far back as 1957 in the literature and can't find one.
Clayden showed a rough scheme but it has hydrogen gas as the H-donor.
I may just be missing it and I'd really appreciate it if somebody can point a reference to me (or better yet
suggest some steps..)
thanks in advance.
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There is some evidence that it is a radical mechanism (at least for related reactions with Pd/C), but you could also draw it with Pd-hydrides. You can inhibit the reaction by adding SET inhibitors, which points to radical intermediates.
see: Tetrahedron 2004, 7973.