Comments on: Epoxides – The Outlier Of The Ether Family https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/ Mon, 17 Nov 2025 17:53:22 +0000 hourly 1 https://wordpress.org/?v=6.9.4 By: James Ashenhurst https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-780983 Mon, 17 Nov 2025 17:52:51 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-780983 In reply to Amy.

You are right. It requires a lot of heat and strong acid. I adjusted the article to reflect this.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-780982 Mon, 17 Nov 2025 17:50:16 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-780982 In reply to AH.

It can be done. One way is to use low valent tungsten.
https://orgsyn.org/demo.aspx?prep=cv7p0121

Another is through using PPh3
https://pubs.acs.org/doi/10.1021/acs.orglett.4c02207

Rhenium is another option:
https://pubs.acs.org/doi/10.1021/acs.orglett.5b01583

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-780980 Mon, 17 Nov 2025 17:40:31 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-780980 In reply to amyar amyr.

Yes, that is acidic cleavage of ethers.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-780979 Mon, 17 Nov 2025 17:39:53 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-780979 In reply to Shashank.

They are not creative commons, but use with a link back.

]]> By: AH https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-737567 Mon, 28 Apr 2025 14:39:35 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-737567 How do you back from an epoxide to an alkene?

]]> By: Shashank https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-603194 Tue, 06 Jul 2021 09:40:17 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-603194 Do these pictures come under creative commons? Can I use this on my website?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-599874 Fri, 16 Apr 2021 20:25:20 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-599874 In reply to Mary.

Epoxides do have ring strain, but they can still form. The nucleophile (alkoxide) is in close proximity to the electrophile so ring formation is quite fast.

]]> By: Mary https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-599752 Mon, 12 Apr 2021 15:33:27 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-599752 Why epoxidation is happened in halohydrin cyclization while the angle pressure will arise?

]]> By: amyar amyr https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-588607 Tue, 24 Nov 2020 13:31:02 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-588607 in the case of di ethyl ether in aqueous solution (H3O+) , in fact there is a reaction where the H2O act as the Nu- !! leading to the formation of 2 eq of ethanol , isn’t ??

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/#comment-552555 Sat, 13 Apr 2019 09:00:02 +0000 https://www.masterorganicchemistry.com/?p=8703#comment-552555 In reply to AJ.

I did – it’s here. https://www.masterorganicchemistry.com/2013/04/02/alkene-addition-pattern-3-the-concerted-pathway/ Epoxidation of aliphatic alkenes is “syn” addition ; both new C-O bonds are formed on the same face of the alkene. This is true regardless of whether you have a cis or trans alkene.

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