December 27, 2024, 01:51:54 AM
Forum Rules: Read This Before Posting


Topic: hydrogenolysis of N-benzyl group using Pd on C, cyclohexene and methanol  (Read 7734 times)

0 Members and 1 Guest are viewing this topic.

Offline xyzi

  • New Member
  • **
  • Posts: 5
  • Mole Snacks: +0/-0

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.

Offline movies

  • Organic Minion
  • Retired Staff
  • Sr. Member
  • *
  • Posts: 1973
  • Mole Snacks: +222/-21
  • Gender: Male
  • Better living through chemistry!
Re: hydrogenolysis of N-benzyl group using Pd on C, cyclohexene and methanol
« Reply #1 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.

Sponsored Links