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This is a question that has bothered me for some time.I have always thought that the part of one molecule will only attack part of another molecule if it has a higher positive charge.So with this in mind, why does the alkene double bond attack the $\ce{O}$ atom of $\ce{OsO4}$. Isn’t the $\ce{O}$ atom negatively charged?

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    $\begingroup$ I am not sure whether it is the alkene that initiates bond formation. However, take a look at the mechanism. It is a cycloaddition. For all we know, the oxygen from the osmium tetroxide may be the one initiating the formation of the bond. I will try to look some journals and post what I find. $\endgroup$ – CoffeeIsLife Dec 8 '16 at 4:29
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    $\begingroup$ Not all reactions are driven by simple attraction of oppositely charged atoms. Consider alkene hydrogenation, acetylene trimerization, or the Diels–Alder thing. $\endgroup$ – Ivan Neretin Dec 8 '16 at 5:59
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Yes. But check the formal charge on the Osmium. It is so very positive that it actually steals electron density from the Oxygen.

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