Staudinger reaction primary amine preparation

Staudinger and Kupfer2 discovered a very interesting method for the preparation of diazomethane. They observed that when the isonitrile reaction of primary amines was applied to hydrazine, diazomethane,3 and not the expected di-isocyanogen, C=N—N=C, was produced in the manner indicated in the following equations ... 

Staudinger reaction),615 H2 and a catalyst, Mg or Ca in MeOH,616 N2H4-Pd,617 and tin complexes prepared from SnCl2 or Sn(SR)2.6l i This reaction, combined with RX — RN3 (0-61). is an important way of converting alkyl halides RX to primary amines RNH, in some cases the two procedures have been combined into one laboratory step.61 Sulfonyl azides RS02N, have been reduced to sulfonamides RSO NH2 by irradiation in isopropyl alcohol620 and with NaH.621... 

---