Lecture 24 - The desired trans isomer can be made using a...

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1 Reading for Monday 3/28 Chapter 21: 21.14-21.17 Mon. 6:00-7:30 pm MAL 3092 Tues. 2:30-4:00 PM MAL 2007 Wed. 5:00-6:30 PM MAL 2001 Thurs. 9:30-10:50 AM MAL 1003 Sat. 11:30 AM-1:00 PM MAL 2007 PLUS Sessions THIS WEEK The Wittig Reaction (21.10) C=O converted to C=C Wittig reagent ( an ylide ) is an organophosphorus compound Mixtures of E/Z isomers can form; cis- often favored over trans- using the classic version of the reaction (i.e. the one we are studying). Capsaicin What makes peppers HOT O N H HO O CH 3 Reaction is under KINETIC control! (oxephosphetane formation is irreversible)
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Unformatted text preview: The desired trans isomer can be made using a variation of the Wittig reaction Application of the Wittig Reaction Reaction is under THERMODYNAMIC control (oxephosphetane formation is reversible, because ylide is highly stabilized by conjugation) 2 Imines (21.11) Formed in reaction between a 1 amine and an aldehyde or ketone Requires mild acidic conditions C=O converted to C=N Reaction reverses in strong acid pH-rate profile for imine formation...
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This note was uploaded on 10/24/2011 for the course CHEMISTRY 623 taught by Professor Benson during the Spring '11 term at Kansas.

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Lecture 24 - The desired trans isomer can be made using a...

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