pset4 - Massachusetts Institute of Technology Organic...

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Massachusetts Institute of Technology Organic Chemistry 5.13 October 13, 2006 Prof. Timothy F. Jamison Problem Set #4 Due Friday, October 20, 12:05 p.m., in lecture (before lecture) 1. Treatment of compound 1 below with a strong base (e.g., n -BuLi) gives a heterocycle with a 5- membered ring treatment with a weak acid (work-up). Account for the relative stereochemistry observed in the product. N N HN N -BuLi 1 2. Propose a mechanism for the reaction below that involves a thermal 4 π electrocyclic ring closure. Clearly indicate the relative stereochemistry in all intermediates. O Me O Me catalytic H + 3. Based on the photochemical and thermal electrocyclic reactions of compound 2 below, comment on the nature of the π system in its 9-membered ring. Account for the relative stereochemistry observed in each of the two reactions. 4. Heating compound 3 below at reflux in toluene in the presence of methyl acrylate affords two products, A and B in a 1:1 ratio of diastereomers . With a catalytic amount of base,
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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pset4 - Massachusetts Institute of Technology Organic...

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