Bingel reaction

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The Bingel reaction in

steric strain
.

The reaction is of importance in the field of chemistry because it allows the introduction of useful extensions to the fullerene sphere. These extensions alter their properties, for instance solubility and electrochemical behavior, and therefore widen the range of potential technical applications.

Bingel reaction.

Reaction mechanism

The

nucleophilic aliphatic substitution in an intramolecular ring cyclopropane
ring closure.

electron withdrawing group, L leaving group

Scope

The Bingel reaction is a popular method in fullerene chemistry. The

tetrabromomethane or iodine.[2] The reaction is also known to take place with the ester groups replaced by alkyne groups in dialkynylmethanofullerenes.[2]

DBU in toluene
at room temperature 45% yield.

An alternative to the Bingel reaction is a fullerene diazomethane reaction. N-(Diphenylmethylene)glycinate Esters [3] in a Bingel reaction take a different conjugate course and react to a fullerene dihydropyrrole.

Bingel reaction with N-(Diphenylmethylene)glycinate Ester

Retro-Bingel reaction

Protocols exist for the removal of the methano group based on

electrolytic reduction[4][5] or amalgamated magnesium.[6]

References

  1. doi:10.1002/cber.19931260829
    .
  2. ^
    PMID 15281772
    .
  3. PMID 16209611
    .
  4. doi:10.1002/(SICI)1521-3773(19980803)37:13/14<1919::AID-ANIE1919>3.0.CO;2-X
    .
  5. PMID 12790625
    .
  6. doi:10.1039/a909704j
    .
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