Wittig reaction

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The Wittig reaction is an organic reaction used to convert a primary or

secondary alkyl halide and an aldehyde or ketone to an olefin using
triphenylphosphine and base. The mechanism beings with attack of the PPH3
on the alkyl halide which releases the halide anion and forms a phosphonium
ion. The base then deprotonates at the alpha position to afford a
phosphonium ylide. The ylide subsequently attacks the alde-hyde or ketone to
form a zwitterion where the oxygen anion then attacks the phosphonium
cation to form an oxaphosphetane. A rearrangement then generates the final
olefin product and releases a triphenylphos-phine oxide by-product whose
formation of a strong P=O bond is the driving force for this reaction.[1][2]

Mechanism

References:

1. Wittig, G.; Schöllkopf, U. Chem. Ber. 1954, 87, 1318–1330.

2. Wittig, G.; Haag, W. Chem. Ber. 1955, 88, 1654–1666.

Other Substitution Reactions:

1/1