Compound 1 undergoes a thermal elimination of nitrogen at 250C to form nitrile 4 (Org
Chapter 6, Problem 6.63(choose chapter or problem)
Compound 1 undergoes a thermal elimination of nitrogen at 250C to form nitrile 4 (Org. Lett. 1999, 1, 537539). One proposed (and subsequently refuted) mechanism for this transformation involves intermediates 2 and 3: N N R1 NH2 R2 N N N R1 N R2 R1 R2 N N H2N C R1 R2 1 4 H H H H 3 2 N N N N N N @ ! (a) Draw curved arrows that show the conversion of 2 to 3. (b) To determine whether or not the proposed mechanism operates, one of the nitrogen atoms was isotopically labeled as 15N, and its location in the product was determined. The absence of 4b in the product mixture demonstrates that the proposed mechanism is not operating. Using resonance structures, explain why the proposed mechanism predicts that 4b should be formed. N N N 1 4a 4b N R1 R2
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