Interaction | Reaction | Process     Data Page

Thioanions and thiols attack cyanogen bromide at bromine to give the corresponding thiobromide, R-S-Br.

The thiobromide is attacked by a second thioanion at sulfur to give the symmetrical R-S-S-R disulfide.

In this reaction the sulfur is oxidised.

2
R–SH
  +  
N≡C–Br
         
R–S–S–R
  +  
HCN
  +  
HBr
Reactant Page Go To Go To
Thiol (generic)     Reactions Using    Reactions Forming
Cyanogen bromide     Reactions Using    Reactions Forming
Disulfide, organic (generic)     Reactions Using    Reactions Forming
Hydrogen cyanide     Reactions Using    Reactions Forming
Hydrogen bromide     Reactions Using    Reactions Forming

Interaction, Reaction, Process defined as:
Multistep: LA/B mechanism
Psudohalogens, Reactions of
Redox
Substitution: Nucleophilic Second Order

© Mark R. Leach 1999 –


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