• The first half of this reaction forms a nitrosamine. From this a diazo compound is formed. After this has left the shift of an 'R' group occurs.
• Which 'R' group migrates depends on the migratory aptitudes of the various groups available.
• Versions of this reaction using diazonium salts which are derived from 2-amino alcohols are called Tiffeneau-Demjanov reactions.
• Diazo compounds are often prone to loss of nitrogen, because the triple bond is so strong. Formation of this bond is the driving force for many nitrogen functional group reactions, for example the Balz-Schiemann reaction, the Sandmeyer reaction, the Tiffeneau-Demjanov reaction and the Wolff-Kischner reaction.
  
  
  References:
• Marson C.M.; Oare C.A.; McGregor J.; Walsgrove T.; Grinter T.J.; Adams H.; Tetrahedron Letters, 2003, Volume 44, Issue 1, 141-143
• Magnus P.; Diorazio L.; Donahoe T.J.; Giles M.; Pye P.; Tarrant J.; Thom S.; Tetrahedron, 1996, Volume 52, Issue 45, 14147-14176