Piancatelli rearrangement
Encyclopedia
In 1976, The Italian chemist G. Piancatelli and co-workers develop a new method to synthesize the 4-hydroxycyclopentenone
Cyclopentenone
Cyclopentenone is a hydrocarbon with chemical formula 56 and CAS number 930-30-3. It is structurally similar to cyclopentanone, with the additional feature of α-β unsaturation in the ring system. Cyclopentenone belongs to the cycloalkene class of compounds and is also a ketone...

derivatives from suitable 2-furylcarbinols through an acid-catalyzed rearrangement (Scheme 1).
The mechanism of this reaction is believed to be a 4-pi electrocyclization, analogous to the Nazarov cyclization,.
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