Home > Community > Mechanism for reaction of NOCl (Tilden reagent) with primary amines
Upvote

31

Downvote
+ Amines
+ Chemistry
Posted by
Marty Silvia

Mechanism for reaction of NOCl (Tilden reagent) with primary amines

According to The Pearson Guide To Organic Chemistry For The IIT JEE by Atul Singhal, the reaction between $\ce{NOCl}$ and $\ce{CH3CH2-NH2}$ is as follows:

$$\ce{CH3CH2-NH2 + NOCl -> CH3CH2Cl + N2 + H2O}$$

But how exactly does the reaction proceed?

The first step (what I think) could be that $\ce{NOCl}$ dissociates into $\ce{NO+}$ and $\ce{Cl-}$ ions and then the $\ce{Cl-}$ ion attacks the amine group and replaces it by $\mathrm{S_N2}$ mechanism.

But according to paperplane.io (via the Internet Archive), a diazonium product is produced. Even though a diazo product is formed, how does it produce an alkyl halide according to my textbook?

Related Posts

33  Upvotes · 2 Comments
16  Upvotes · 3 Comments
15  Upvotes · 8 Comments
17  Upvotes · 8 Comments
16  Upvotes · 10 Comments
TOP