dean stark - 22-4-2011 at 06:26
I'm thinking there are two ways to (di)cyclopentadiene from e.g. tricyclodecenyl acetate...
1. Pyrolysis
The temperature for pyrolysis of secondary esters is supposed to be lower than primary, but according to cv5p0235 the temperature can still be pretty high (700ºC in that case). I guess the high temperature would also induce retro Diels-Alder,
yielding cyclopentadiene.
2. Hydrolysis then dehydration
Base catalysed hydrolysis followed by acid-catalysed dehydration. Might be a bit more straight-forward due to fewer variables (e.g. conditions of
pyrolysis).
Main problem is that I don't have any specifics. Most of my searches return with the arrow in the opposite direction (creating the ester from the acid
and dicyclopentadiene).
Any comments or references are really appreciated! Am I on the right track?