31. Periodate Cleavage, Retrosynthesis, and Green Chemistry

Update: 2012-04-02

Description

The ability of periodic acid (HIO4) to cleave the C-C bond of vicinal diols and [gr]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.

Complete course materials are available at the Open Yale Courses website: http://oyc.yale.edu

This course was recorded in Spring 2011.

Comments

In Channel

34. Acids and Acid Derivatives

2012-04-0250:28

27. Triphenylmethyl and an Introduction to Carbonyl Chemistry

2012-04-0200:02

6. Brønsted Acidity and the Generality of Nucleophilic Substitution

2012-04-0200:02

38. Review: Synthesis of Cortisone

2012-04-0200:03

37. Proving the Configuration of Glucose and Synthesizing Two Unnatural Products

2012-04-0200:03

36. [gr]α-Reactivity and Condensation Reactions

2012-04-0200:03

33. Green Chemistry. Acids and Acid Derivatives

2012-04-0200:02

35. Acyl Insertions and [gr]α-Reactivity

2012-04-0200:02

32. Measuring Bond Energies: Guest Lecture by Prof. G. Barney Ellison

2012-04-0200:02

30. Oxidation States and Mechanisms

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31. Periodate Cleavage, Retrosynthesis, and Green Chemistry

2012-04-0200:02

29. Imines and Enamines. Oxidation and Reduction

2012-04-0200:03

28. Mechanism and Equilibrium of Carbonyl Reactions

2012-04-0200:02

26. Aromatic Substitution in Synthesis: Friedel-Crafts and Moses Gomberg

2012-04-0200:03

25. C-13 and 2D NMR. Electrophilic Aromatic Substitution

2012-04-0200:03

24. Higher-Order Effects, Dynamics, and the NMR Time Scale

2012-04-0200:03

23. Diamagnetic Anisotropy and Spin-Spin Splitting

2012-04-0200:02

22. Medical MRI and Chemical NMR

2012-04-0200:02

21. Functional Groups and Fingerprints in IR Spectroscopy. Precession of Magnetic Nuclei

2012-04-0200:03

20. Electronic and Vibrational Spectroscopy

2012-04-0200:02

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31. Periodate Cleavage, Retrosynthesis, and Green Chemistry

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31. Periodate Cleavage, Retrosynthesis, and Green Chemistry

J. Michael McBride

31. Periodate Cleavage, Retrosynthesis, and Green Chemistry