[carlituz]

Hi everybody,

I was wondering if it's possible to synthesize cyclopentadiene starting from alpha-pinene commonly found in turpentine oil.
A hypothesis was an isomerization of alpha-pinene to camphene. Camphene should then pass a Retro Diels Alder reaction to give cyclopentadiene and isoprene. Do you think it's possible? And in which conditions (acid, base, catalyst needed)?

Thank you
Carlo

[Enthalpy]

Hi Carlo, welcome!

Independently of the feasibility, I wonder whether this synthesis is economical, because cyclopentadiene too is cheap and abundent as a by-product of naphtha cracking
https://en.wikipedia.org/wiki/Cyclopentadiene

I fear that retro Diels-Alder alone doesn't suffice, because of an imbalance of two hydrogen atoms.
C₁₀H₁₆ camphene and alpha-pinene (terpene)
C₅H₈ isoprene (hemiterpene)
C₅H₆ cyclopentadiene (not a hemiterpene)