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I was wondering if a three membered ring or a three membered epoxide would ever open up spontaneously when exposed to heat, or acids/bases?

I would think at some point, but will it routinely happen to a three membered epoxide?

ATP
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    Well, the whole thing is pretty strained, so yes, it would snap open quite easily. – Ivan Neretin Feb 20 '16 at 20:38
  • Definitely, three membered rings are extremely strained. The bond angle is extremely small. – Saul McShane Feb 20 '16 at 23:48
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    There no other oxiranes (epoxides) but three-membered rings! On the opening with bases, see http://chemistry.stackexchange.com/questions/27288/do-epoxide-rings-react-with-bases/27290, on the opening under acidic conditions see http://chemistry.stackexchange.com/questions/2655/sn1-like-reaction-acid-cataylzed-hydrolysis-of-epoxide and http://chemistry.stackexchange.com/questions/4305/regioselectivity-of-acid-catalyzed-ring-opening-of-epoxides – Klaus-Dieter Warzecha Feb 21 '16 at 18:09
  • I realized I added acids/bases into the question, but could anyone tell me if there is any info on spontaneous opening as heat increases in solution – ATP Feb 25 '16 at 16:01

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