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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

Title: hydrogenolysis of N-benzyl group using Pd on C, cyclohexene and methanol
Post by: xyzi on September 17, 2007, 12:43:35 AM

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.
Title: Re: hydrogenolysis of N-benzyl group using Pd on C, cyclohexene and methanol
Post by: movies on September 27, 2007, 01:37:12 PM
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.