CHEM 125b - Lecture 31 - Periodate Cleavage, Retrosynthesis, and Green Chemistry

Lecture 31 - Periodate Cleavage, Retrosynthesis, and Green Chemistry

Overview

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. Pharmaceutical manufacturers have taken great interest in developing new solvents and reagents that minimize hazards, waste, and environmental impact of traditional reactions.

Resources

Professor McBride's website resource for CHEM 125b (Spring 2011)

https://webspace.yale.edu/chem125/

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