Lesson 1
Wittig Olefination 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-31 License: Creative Commons BY-NC-SA The ability of periodic acid (HIO4) to cleave the C-C bond of vicinal diols and α-hydroxycarbonyl compounds allowed structure determination of sugars and their ketals before spectroscopy was available. Reduction of carbonyl compounds by organometallic or hydride reagents provides a range of schemes for synthesizing various alcohols, where preference may be dictated by the desire to avoid competing processes. Wittig olefination allows conversion of C=O to C=C with good control over constitutional isomerism.

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