Elementary (Hive Addict)
07-04-02 04:25
No 328661
      Benzyl Isocyanide  Bookmark   

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
(Hive Bee)
07-04-02 07:16
No 328705
      undesired byproduct  Bookmark   

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.
(Hive Addict)
07-04-02 07:31
No 328709
      benzylamine to benzyl cyanide !  Bookmark   

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
(Hive Bee)
07-04-02 13:15
No 328809
      experiment  Bookmark   

You'll have to experiment with it to find out for sure if that method will work, but a very clever idea. 
(Hive Prodigy)
07-04-02 14:59
No 328828
      Hey!  Bookmark   

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. smile

(Hive Addict)
07-04-02 15:50
No 328840
      Struggling  Bookmark   

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 500c.

John Lennon - Working Class Hero
(Hive Bee)
07-05-02 08:41
No 329056
      isomerization  Bookmark   

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.