December 24, 2024, 12:04:48 PM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: Mechanism of CN-NH2 cyclization  (Read 3494 times)

0 Members and 1 Guest are viewing this topic.

Offline Rutherford

  • Sr. Member
  • *****
  • Posts: 1868
  • Mole Snacks: +60/-29
  • Gender: Male
Mechanism of CN-NH2 cyclization
« on: October 25, 2013, 11:45:20 AM »
What is the mechanism of the attached reaction? What rearrangements are happening?
Logged

Offline AlphaScent

  • Full Member
  • ****
  • Posts: 644
  • Mole Snacks: +24/-7
  • Gender: Male
Re: Mechanism of CN-NH2 cyclization
« Reply #1 on: October 25, 2013, 02:27:58 PM »
This is an awesome question...  What is more likely to shift a cyano group or an amino group?  Seems like neither, but it has to happen..
Logged
If you're not part of the solution, then you're part of the precipitate

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Mechanism of CN-NH2 cyclization
« Reply #2 on: October 25, 2013, 02:58:20 PM »
It looks like an elimination/addition of cyanide. I don't know if that is a homolytic or heterolytic reaction. The readdition adds the nitrogen to give a net isomerization. You should complete it from there.
Logged
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline Rutherford

  • Sr. Member
  • *****
  • Posts: 1868
  • Mole Snacks: +60/-29
  • Gender: Male
Re: Mechanism of CN-NH2 cyclization
« Reply #3 on: October 26, 2013, 03:54:13 AM »
I don't understand. There are two different nitrogens. Which one adds to what?
Logged

Offline Archer

  • Chemist
  • Sr. Member
  • *
  • Posts: 1001
  • Mole Snacks: +85/-20
  • Gender: Male
Re: Mechanism of CN-NH2 cyclization
« Reply #4 on: October 26, 2013, 07:52:10 AM »
Is this just general interest or part of an assignment?

At least make an attempt at the problem.
Logged
“ I love him. He's hops. He's barley. He's protein. He's a meal. ”

Denis Leary.

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Mechanism of CN-NH2 cyclization
« Reply #5 on: October 26, 2013, 08:49:19 AM »
A heterolytic cleavage is easier to do. Start with the electrons on the nitrogen and form cyanide and a ketamine as the immonium form. Re-add cyanide using the nitrogen.
Logged
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline Rutherford

  • Sr. Member
  • *****
  • Posts: 1868
  • Mole Snacks: +60/-29
  • Gender: Male
Re: Mechanism of CN-NH2 cyclization
« Reply #6 on: October 26, 2013, 09:25:58 AM »
Then it may be something like this.
Logged
Pages: [1]   Go Up
« previous next »
Sponsored Links