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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: strigoi on September 27, 2020, 01:54:45 PM

Title: rxn mechanism for this
Post by: strigoi on September 27, 2020, 01:54:45 PM

To my understanding, iminium nitrogen is drawn to boron and this interactions lets hydride loose and attacks the double bond carbon, dropping the electron on nitrogen and letting boron go. Correct me here if i am wrong.

What i dont understand is whats going on with the carbons that ive drawn black arrows for. These should be hydrated aswell but i dont get it how? Does the double bond reform with nitrogen somehow and one after another BH4 starts loading the carbons or what?

Title: Re: rxn mechanism for this
Post by: Babcock_Hall on September 30, 2020, 10:53:00 AM

The process is a hydrogenation, not a hydration.  That might help.

Title: Re: rxn mechanism for this
Post by: kriggy on October 03, 2020, 03:24:35 PM

After reducing the first double bond, you get activated enamine which can accept hydride as well