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I often read that reactive organometallics must be handled under an inert atmosphere because they react with oxygen in the atmosphere. This applies to grignard reagents, organolithium reagents, and organozinc reagents.

What is the reaction of these organometallics with oxygen? I don't see how oxygen can be electrophilic. Maybe it forms a peroxyacid?

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  • $\begingroup$ Part of the trouble is that the reaction with oxygen is usually very exothermic, so it tends to take place all over your fume hood. I would expect to get a whole range of reactions. $\endgroup$
    – TAR86
    Jan 27, 2020 at 19:01
  • $\begingroup$ A lot of organometallics are sensitive to oxygenation which oxygen is quite good at. $\endgroup$
    – matt_black
    Jan 28, 2020 at 16:39

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Grignards react with molecular oxygen to form hydroperoxides. According to this paper here the yield for alkyl hydroperoxides can be as high as 90%, yields from aryl Grignards are lower (10-20%).

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