December 09, 2024, 04:00:26 PM
Forum Rules: Read This Before Posting


Topic: Wolff Kishner?  (Read 949 times)

0 Members and 1 Guest are viewing this topic.

Offline sharbeldam

  • Full Member
  • ****
  • Posts: 344
  • Mole Snacks: +8/-2
Wolff Kishner?
« on: June 18, 2020, 02:53:47 PM »
Can it reduce ketones that have functional groups in their chain? for instance if there is an amine involvled.
let's say 4-amino-2-pentanone.

are there specific rules for this reaction?

Thank you
O-Chem 1+2 Online Free tutor on Skype: Live:damnitsjake21

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 2304
  • Mole Snacks: +154/-10
Re: Wolff Kishner?
« Reply #1 on: June 19, 2020, 06:59:32 AM »
What would you say about amino groups and ketone-carbonyl groups, can they react with each other in some way?

Offline sharbeldam

  • Full Member
  • ****
  • Posts: 344
  • Mole Snacks: +8/-2
Re: Wolff Kishner?
« Reply #2 on: June 19, 2020, 09:14:53 AM »
Yes to produce amines and enamines, but in general if there was a functional group that doesnt react with the ketone, can we do the wolff kishner or does it have to be alkyl?
O-Chem 1+2 Online Free tutor on Skype: Live:damnitsjake21

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 2304
  • Mole Snacks: +154/-10
Re: Wolff Kishner?
« Reply #3 on: June 20, 2020, 03:27:36 AM »
You use hydrazine fot this, a very strong nucleophile so this will be difficult with electrophilic groups on the molecule.
You can also make a dithioacetal from the ketone/aldehyde and use Raney-Ni to de-sulphurize it, this will give the same result as Wold-Kischner and you avoid strong nucleophile. https://en.wikipedia.org/wiki/Thioacetal
https://en.wikipedia.org/wiki/Raney_nickel

Sponsored Links