Question

Create a mechanism for the following reagents: 1,2,3,4,5,6,7,8-octahydro-napthalene, osmium tetraoxide, and water in order to create...

Create a mechanism for the following reagents: 1,2,3,4,5,6,7,8-octahydro-napthalene, osmium tetraoxide, and water

in order to create cis-octahydro-naphthalene-4a,8a-diol

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Answer #1

Alkenes add to OsO4 to give diolate species that hydrolyze to cis-diols. The net process is called dihydroxylation. This proceeds via a [3 + 2] cycloaddition reaction between the OsO4 and alkene to form an intermediate osmate ester which rapidly hydrolyses to yield the vicinal diol. As the oxygen atoms are added in a concerted step, the resulting stereochemistry is cis. The general mechanism of alkene with OsO4 is described as follow

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