Lesson 1
Ozonolysis and 1,3-Dipolar Cycloaddition 1
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Prof. McBride, J. Michael, CHEM 125b, Freshman Organic Chemistry II, Spring 2011, YALE Open Courses: Yale University, Chemistry (Accessed 16/09/2014), http://oyc.yale.edu/chemistry/chem-125b/lecture-14 License: Creative Commons BY-NC-SA The ozonolysis of alkenes begins with several 1,3-dipolar cycloadditions that can be understood in terms of matching HOMOs with LUMOs of the corresponding symmetry. Although addition to the C=O double bond is usually considered nucleophilic, it can have an important electrophilic component that makes it mechanistically analogous to the "electrophilic" additions to C=C being discussed in these lectures. The use of metals to access orbitals of the proper symmetry is introduced through alkene dihydroxylation via cycloaddition of OsO4.

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