Benzyl Isocyanide

[Elementary]

Or maybe phenylacetonisonitrile ?

Does or can this chemical exist ?

Could it be made like this :

C6H5CH2NH2 + CHCl3 + 3KOH = C6H5CH2NC + 3KCl + 3H2O
John Lennon - Working Class Hero

[Nemo_Tenetur]

Yes, isonitriles exist. They are undesired byproducts in the synthesis from benzylchloride and alkali cyanide. You can destroy the isonitriles with concentrated sulphuric acid. See the "organic syntheses" for a detailed recipe. Isonitrile has a very unpleasant smell.

[Elementary]

I know that isonitriles rearrange themselves to nitriles if heated.

I was thinking of using this as a path to benzyl cyanide from benzylamine.

Toluene/Benzyl Alcohol > Benzyl Chloride > Benzylamine > Benzyl Isocyanide > Benzyl Cyanide > Phenylacetic Acid
John Lennon - Working Class Hero

[Aurelius]

You'll have to experiment with it to find out for sure if that method will work, but a very clever idea.

[PrimoPyro]

Can this be done to an aniline? Ph-NH2 --> Ph-N#C (# = triple bond)

That would be great! Or one could turn a benzylamine of your choosing into the phenethylamine of your choosing by

PhCH2-NH2 --> PhCH2-N#C --> PhCH2-C#N --> PhCH2CH2-NH2 (via reduction)

hmm, 2,5-dimethoxy-N-methyl-aniline --> 2,5-dimethoxy-4-methyl-aniline, and from there to 2CD.  

                                                   PrimoPyro

[Elementary]

I am really struggling to find any details on the rearangement of isonitriles to nitriles (isocyanides to cyanides). I have done extensive patent searching with no results and also comprehensive engine searches with no luck.

All I have is a small passage in an organic chemistry book saying that, on heating isonitriles undergo rearrangement, forming nitriles.

Another interesting thing I found :

A newer method of synthesizing nitriles is to pass the vapour of the carboxylic acid or its ester, mixed with ammonia, over heated alumina at 500°c.
John Lennon - Working Class Hero

[Aurelius]

Try heating the isonitriles in a high boiling suitable solvent (water free, and non-reactive with the isonitrile or the product)  at temps around 180-220*C for a couple of hours then test however you can.