2311 lec 13 - GreenOxidationofBorneol to CamphorusingOxone...

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Green Oxidation of Borneol to Camphor using Oxone® 3 3 3 0.5 equivalents Oxone cat. NaCl Ethyl acetate/H 2 O 3 3 3 (1 S )-Borneol (1 S )-Camphor
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Goals of Experiment NEW experiment! Very first time it is being run in an organic lab course “Green” chemistry–Use of Oxone® and NaCl instead of toxic chromium reagents Synthesizing a product for use in an organic chemistry research group! Constructing a homemade desiccator to dry the product Sublimation as a purification technique! Learn about TERPENE natural products
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History of Camphor Isolation documented as early as the ninth century! Culinary and medicinal uses Common modern uses: ± Medicinal as antimicrobial and anesthetic (with menthol), vapor steam products like Vicks Vapor rub, cough suppressant ± Plasticizer (cellulose nitrate) ± Embalming fluid ± Pyrotechnics (fireworks) ± Moth repellent ± Preservative in pharmaceuticals and cosmetics
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" " head tail Limonene (lemons) Terpene Natural Products > 20,000 known All have “isoprene” repeating unit and multiple of 5 carbons
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Chirality in Terpene Natural Products (1 S )-camphor L-camphor (-)-camphor O O (1 R )-camphor D-camphor (+)-camphor
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Chiral Catalysts from Camphor O (1 R )-camphor D-camphor (+)-camphor MeO 2 C O MeO 2 C H 2 N HOOC I
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This note was uploaded on 02/20/2010 for the course CHEM 2311 taught by Professor Wissinger during the Spring '10 term at University of Minnesota Duluth.

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2311 lec 13 - GreenOxidationofBorneol to CamphorusingOxone...

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