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Fundamentals of Organic ChemistryChemistryAmines

Identify the major product formed in the following reaction.

Correct answer

1

Step-by-step solution

Fluorene is deprotonated by one equivalent of BuLi to generate the fluorenyl anion. The fluorenyl anion attacks one of the carbonyl groups of N -tosyloxyphthalimide, leading to ring opening and the formation of a 2-(9-fluorenylcarbonyl)- N -tosyloxybenzamide intermediate. Under the basic conditions, this intermediate undergoes a Lossen rearrangement. The aryl group migrates to the nitrogen atom with the elimination of the tosylate group, yielding 2-(9-fluorenylcarbonyl)phenyl isocyanate. The second equivalent of Bu

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