Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Tricyclodecenyl ester to (di)cyclopentadiene via elimination?
dean stark
Harmless
*




Posts: 12
Registered: 17-3-2011
Member Is Offline

Mood: No Mood

[*] posted on 22-4-2011 at 06:26
Tricyclodecenyl ester to (di)cyclopentadiene via elimination?


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 (700ÂșC 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?
View user's profile View All Posts By User

  Go To Top