As shown below, compound 1 can be transformed to compound

Chapter 17, Problem 17.79

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As shown below, compound 1 can be transformed to compound 2, which undergoes a thio-Claisen rearrangement (similar to a Claisen rearrangement, but with sulfur instead of oxygen) to give compound 3 (J. Am. Chem. Soc. 2000, 122, 190191). N Ph Ph S 1) BuLi 2) Br 1 N Ph Ph S 3 2 ThioClaisen ? (a) Identify the structure of compound 2, which contains a carboncarbon p bond in the Z configuration. (Hint: Work backward from compound 3.) (b) Propose a plausible mechanism for the transformation of 1 to 2. (c) Offer an explanation for the stereochemical outcome that is observed with respect to the newly formed chirality center. (Hint: You might find it helpful to use a molecular model set.)

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