Lecture 13 - Addition to Form Three-Membered Rings: Carbenoids and Epoxidation

author: J. Michael McBride, Department of Chemistry, Yale University
recorded by: Yale University
published: Aug. 19, 2014,   recorded: March 2011,   views: 1635
released under terms of: Creative Commons Attribution No Derivatives (CC-BY-ND)

See Also:

Download Video - generic video source Download yalespan125bs2011_mcbride_lec13_01.mp4 (Video - generic video source 588.3 MB)

Download Video Download yalespan125bs2011_mcbride_lec13_01_640x360_h264.mp4 (Video 152.6 MB)

Download subtitles Download subtitles: TT/XML, RT, SRT

Help icon Streaming Video Help

Related Open Educational Resources

Related content

Report a problem or upload files

If you have found a problem with this lecture or would like to send us extra material, articles, exercises, etc., please use our ticket system to describe your request and upload the data.
Enter your e-mail into the 'Cc' field, and we will keep you updated with your request's status.
Lecture popularity: You need to login to cast your vote.


After drill on the mechanism of the pinacol rearrangement, this lecture applies molecular-orbital analysis to simultaneous electrophilic/nucleophilic attack by a single atom to form a three-membered ring from an alkene. These reactions provide drill in consistent use of the curved-arrow formalism for describing electron-pair shifts. Two alternative mechanisms for formation of cyclopropanes by the alkylzinc Simmons-Smith "carbenoid" reagent are proposed, and the one-step mechanism is supported by theory. Epoxidation of alkenes by peroxycarboxylic acids also seems to go by way of a concerted electrophilic/nucleophilic process involving a single transition state. The stereochemistry and scale of various paths to epoxides is discussed in the context of their commercial utility.

Link this page

Would you like to put a link to this lecture on your homepage?
Go ahead! Copy the HTML snippet !

Write your own review or comment:

make sure you have javascript enabled or clear this field: