[Nescafe]

Hi,

What is the salt you generate after the reduction of the imine with NaCNBH₃ or Na(OAc)₃H? Basically I am curious to know after the hydrogen attacks the imine what happens to the reagent?

Na⁺ NC-B^-H₃ ---> NC-B^-H₂ what is the counter ion for Na now? CN?

Cheers,

Nescafe.

[Dan]

Add the imine to your reaction equation and you should see it. Note that these reactions are normally carried out in acetic acid.

[Nescafe]

So you get Na OAc and what happens to the NC-BH₂? just floats around by itself I am guessing...

[NotExactly]

It would depend on the solvent you run the reaction in.  In the case of acetic acid it would be NaB(OAc)H2.  In the case of MeOH it would be NaB(OCH3)H2

[Nescafe]

Do you mean NaCN-B(OAc)H2 and NaCNB(OCH3)H2?

[NotExactly]

No I dont.  I mean Na+ [BCN(OAc)H2]-.  Minus charge is on the boron.  cyano, acetate, and hydrides on the boron. 

[Nescafe]

It would depend on the solvent you run the reaction in.  In the case of acetic acid it would be NaB(OAc)H2.  In the case of MeOH it would be NaB(OCH3)H2

I was just pointing out that in you original answer you missed the CN all together

[NotExactly]

It would depend on the solvent you run the reaction in.  In the case of acetic acid it would be NaB(OAc)H2.  In the case of MeOH it would be NaB(OCH3)H2

I was just pointing out that in you original answer you missed the CN all together

Doh!  You are correct sir.  Nice catch.