Borodin reaction

Heinz and Clare Hunsdiecker converted Borodin s synthesis into a general method, the Hunsdiecker or Hunsdiecker-Borodin reaction. Borodin was also an accomplished composer and is now best known for his musical masterpiece, opera Prince Egor. He kept a piano outside his laboratory. 

Hunsdiecker Reaction (Borodine Reaction, Borodine-Hunsdiecker Reaction)... 

For example, 2-bromoquinuclidine (80) does not form Grignard reagents and 2-aminoquinuclidine is so unstable that on hydrolysis of its urethans (81) under mild conditions ammonia is lost and polymers of dehydroquinuclidine are formed. The synthesis of 2-bromoquinuclidine (80) was achieved by the Borodin reaction,90 and the urethans (81) were obtained from quinuclidine-2-carboxhydrazide (82) by the Curtius reactions.142 The Curtius reaction with quinucli-dine-4-carboxylic acid derivatives gave 4-aminoquinuclidine (83).143 This compound (83) was also synthesized directly from quinuclidine-4-carboxylic acid by the Schmidt reaction. However, the first method is better, in spite of having more steps. 

Naskar, D., Chowdhury, S., Roy, S. Is metal necessary in the Hunsdiecker-Borodin reaction Tetrahedron Lett. 1998, 39, 699-702. 

The Hunsdiecker reaction is the reaction of silver carboxylate 1 with bromine to give bromide 2 at elevated temperature.1The reaction also works for making chlorides and iodides. It is also known as the Hunsdiecker-Borodin reaction. 

There are other functional group transformations that lead to alkyl halides. A classical transformation converts carboxylates to allyl bromides (C—CO2 C—Br). This transformation is called the Hunsdiecker reaction (jt jjag also been called the Borodin reaction) 3 and it is most useful for the preparation of econdary halides. The silver salt of a carboxylic acid is heated with bromine to give the bromide via decarboxylation. An example is conversion of the silver salt of cyclohexane carboxylic acid (163) to bromo-cyclohexane.1 4 Phosphorus and bromine also react with acids in the Hell-Volhard-Zelinsky reaction. 

---