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