The Dark Carbon Rises
Compound E reacts with atomic Carbon to give F. Knowing that F is a hydrocarbon with
and that after deprotonation, the anion is aromatic and has only 4 signals in H-RMN, find the number of signals for F in H-RMN.
Hint: C is a diol and E has 4 double bonds.
The answer is 7.
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1 solution
The sequence of reactions is as follows : Birch reduction ( the reduced double bond is the one between the carboxylic groups), Acyloin condensation, reduction of the carbonil group, Corey reduction of the diol which leaves a double bond so D is bicyclo[4,2,0]octa-2,4,7-triene; ring-opening to COT and reaction with atomic carbon followed by a rearrangement to indene.