Kauffmann olefination

The reagent was generated in situ by conversion of different halogenides of molybdenum or tungsten with methyllithium at low temperatures (−78 °C).

Mechanism experiments shows that the olefination process is a sequence of cycloaddition and cycloelimination steps.

For a long time this reaction had no applications in synthetic organic chemistry.

In 2002 it was used in a total synthesis of the terpene gleenol as a mild and non-basic reagent in a one-pot-protocol with an olefin metathesis step with Grubbs catalyst.

[5] It is remarkable that the organometallic catalyst tolerates the inorganic reaction products.