Prévost reaction

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The Prévost reaction is

anti stereochemistry.[1][2][3] The reaction was discovered by the French chemist Charles Prévost
(1899–1983).

The Prévost reaction
The Prévost reaction

Reaction mechanism

The reaction between silver benzoate (1) and iodine is very fast and produces a very reactive iodinium benzoate intermediate (2). The reaction of the iodinium salt (2) with an

neighboring group substitution of the benzoate ester to give the oxonium salt (5). A second SN2 substitution
by the benzoate anion gives the desired diester (6).

The mechanism of the Prévost reaction
The mechanism of the Prévost reaction

In the final step

syn addition
.

References

  1. Comptes rendus
    . 196: 1129.
  2. ^ Charles Prévost; C.A. 27, 3195 (1933)
  3. .

See also