Interaction | Reaction | Process     Data Page

An aldoses can be chain extended to a diastereomeric mixture of the two higher aldoses by Kiliani-Fischer synthesis.

HCN is added to the aldehyde function which is reduced to the imine (Pd on barium sulfate catalyst) and then hydrolysed to the chain extended aldehyde. This synthesis is of academic interest and is not of industrial importance.

The reverse reaction, the chain shortening by one carbon via oxidation, is known as Ruff degradation.

P. Yurkanis, Organic Chemistry 3rd ed., Prentice Hall (2001)

2
  +  
2
HCN
  +  
2
H2
  +  
Pd
on BaSO4
  +  
2
H2O
          
  +  
Reactant Page Go To Go To
D-Arabinose     Reactions Using    Reactions Forming
Hydrogen cyanide     Reactions Using    Reactions Forming
Hydrogen     Reactions Using    Reactions Forming
Palladium on barium sulfate Catalyst    Reactions Using    Reactions Forming
Water     Reactions Using    Reactions Forming
D-(+) Glucose     Reactions Using    Reactions Forming
D-Mannose     Reactions Using    Reactions Forming

Interaction, Reaction, Process defined as:
Addition: Electrophilic Protonation
Chain Extension
Hydrogenation, catalytic
Hydrolysis
Name Reaction

© Mark R. Leach 1999 –

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