Comments on: Epoxide Ring Opening With Base https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/ Tue, 08 Aug 2023 14:42:21 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-665986 Tue, 08 Aug 2023 14:42:21 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-665986 In reply to Narsis.

By aluminum butoxide, could you be more specific? Do you have an exact example you are thinking of, or are you referring to one or more of the examples in the post.

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By: Narsis https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-665667 Sat, 05 Aug 2023 10:36:48 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-665667 what is the epoxides ring opening with aluminum butoxide?
How does aluminum butoxide catalyze this reaction?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-597212 Thu, 28 Jan 2021 16:46:45 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-597212 In reply to Archie.

Generally NaBH4 is not a strong enough nucleophile to react with epoxides. You need a counter-ion that is more strongly coordinating to oxygen. LiAlH4 will work.

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By: Archie https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-597119 Wed, 27 Jan 2021 13:18:18 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-597119 Hi, what would happen if an epoxide is reacted with NaBH4 in the presence of EtOH, would the NaBH4 act as a nucleophile and then the EtOH would attatch? Thanks

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By: James Ashenhurst https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-572304 Wed, 04 Dec 2019 19:10:58 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-572304 In reply to Alex.

Generally not. Even though it would release ring strain, you’d be going from a very weak base (Br-) to a much stronger base (O- ) if bromide ion opened the epoxide. Furthermore, even if it did, the reverse reaction would easily occur – recall that epoxides are formed from the closure of deprotonated halohydrins!
https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/
You really need the presence of an acid to stop the reaction at the halohydrin stage.

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By: Alex https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-572231 Wed, 04 Dec 2019 04:04:14 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-572231 Would NaBr work in basic conditions?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-550235 Mon, 18 Mar 2019 21:26:42 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-550235 In reply to Aditesh Upadhyay.

Is LiAlH4 even compatible with AlCl3 ? I’ve never seen those two reagents used together.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-550234 Mon, 18 Mar 2019 21:25:56 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-550234 In reply to laksheya.

If it’s useful to you – great!

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By: James Ashenhurst https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-550233 Mon, 18 Mar 2019 21:25:30 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-550233 In reply to Piyush.

That’s not really the opening of an epoxide with a base. There, you’re trying to coordinate the epoxide oxygen to the electrophilic phosphorus, forming a transient ion pair that will release chloride ion and open the epoxide. Kind of beyond the scope of what we deal with here.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2015/02/10/opening-of-epoxide-with-base/#comment-550232 Mon, 18 Mar 2019 21:24:16 +0000 https://www.masterorganicchemistry.com/?p=8738#comment-550232 In reply to Beth.

I’m not certain how to answer your question without a diagram. If you’re looking for selectivity between opening two epoxides, that will be difficult to achieve with NaOH unless there is a clear steric or electronic preference favoring one attack versus the other.

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