Chem 634 PS2 2006 Prof Fox 1 Provide a mechanism OMe RN Pd 0 H O RN MeO I H OH 2 Predict the product Explain your choice H H Pd 0 Br D H D H H Et3N D 3 Reaction of 1 with mCPBA gives intermediate 2 Subsequent reaction with NaCN gives 3 What is the structure of 2 Explain your reasoning based on what you know about epoxide opening reactions H OH H NaCN mCPBA 2 1 H 1 H OH CN OH 4 The amination reaction of chloride 1 with amine 2 is faster than the corresonding reaction with bromide 3 However when equimolar amounts of 1 2 and 3 are combined adduct 5 is the major product Explain how this is possible O Pd 0 O Cl N NaOtBu reaction complete in 1 h at 80 C N P tBu 2 H 4 1 2 just a ligand N NaOtBu N H 2 3 O Pd 0 O Br only 29 conversion after 1 h at 80 C P tBu 2 5 but Pd 0 Br 3 1 equiv Cl 1 1 equiv O N H 2 1 equiv O NaOtBu O N N P tBu 2 80 C 5h 5 97 4 3 5 Reading assignment from the Primary Literature provide a brief synopsis hand drawn structures of a paper from the primary chemical literature Organic Letters and Tetrahedron Letters are the most appropriate sources for papers Select an article that describes a new type of synthetic methodology In addition to outlining the main idea of the paper I ask that you make a list at the bottom of reactions concepts learned by reading this paper
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