New reductive addition of hard nucleophiles to 6,7-bis(methylsulfanyl)-1,4-dihydro-1,4-methanonaphthalene-5,8-dione
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2000-01-01
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Royal Soc Chemistry
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A new reaction mode of 6,7-bis(methylsulfanyl)-1,4-dihydro-1,4-methanonaphthalene-5,8-dione 1 with the hard nucleophiles sodium benzene- or methane-sulfinate and cyanide, in DMSO, at room temperature, leads to the unexpected hydroquinonoid products 3a-c. All the data are in agreement with a mechanistic pathway involving the initial attack of the hard nucleophile onto the hard carbonyl group, followed by a symbiotic re-attack of the oxygen on the incoming group. In the case of soft nucleophiles, reaction on the olefinic carbon of the enedione system is preferential.
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Journal Of The Chemical Society-perkin Transactions 1. Cambridge: Royal Soc Chemistry, n. 21, p. 3692-3694, 2000.
