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Topic: Epoxidation of naphthalene  (Read 2258 times)

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Offline Rutherford

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Epoxidation of naphthalene
« on: January 05, 2016, 06:16:23 AM »
How to achieve the attached transformation? I thought about epoxidation with CF3COOOH, the weakest bond reacts and that's the one connecting the rings. Opening of the epoxide with KOH in DMSO would afford the anti diol. Then, is it better to reduce the dienes with Na in ammonia or hydrogenation?
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Offline discodermolide

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Re: Epoxidation of naphthalene
« Reply #1 on: January 05, 2016, 06:22:34 AM »
Don't think you can epoxidise naphthalene, it's too aromatic for that. Phenanthrene, yes. But that does not *delete me*
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Offline Rutherford

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Re: Epoxidation of naphthalene
« Reply #2 on: January 05, 2016, 06:31:09 AM »
Ah okay. I saw it reacts with carbenes at that bond so I thought it would epoxidize. Then it's 1st Birch reduction then epoxidation.
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