CRUSTY
Hazard to Others
Posts: 139
Registered: 5-6-2016
Location: Nearby
Member Is Offline
Mood: High-Order
|
|
Friedel-Crafts Alkylation using iodine
Hello all, bit of a beginner question. I was wondering, would it be possible to do a successful FC alkylation of benzene using iodine, despite the low
electronegativity of iodine relative to carbon. I'm mostly asking this because of the lower toxicity and higher melting/boiling points of iodine
compared to other halogens. I won't be surprised if the answer to all of this is no, but I couldn't find anything mentioning this on the search
engine.
[Edited on 16-7-2016 by CRUSTY]
|
|
|
AvBaeyer
National Hazard
Posts: 645
Registered: 25-2-2014
Location: CA
Member Is Offline
Mood: No Mood
|
|
I am unaware of iodine catalyzed "alkylations" in the F-C sense. However, acylations to give ketones (acetic anhydride + iodine) were shown to be
possible if the aromatic substrate is reactive enough. Anisole, furan, and thiophene are known to give the acyl derivatives. I do not have the
references immediately at hand but the work was done in the 1950's. I know that one of the investigators was RM Dodson so you could track that down if
you are interested. I have tried some of these iodine catalyzed acylations and they are a real mess with multiple products. They seem to be quite
sensitive to a broad range of reaction conditions. Perhaps that is why interest quickly withered.
AvB
|
|
|
CRUSTY
Hazard to Others
Posts: 139
Registered: 5-6-2016
Location: Nearby
Member Is Offline
Mood: High-Order
|
|
Quote: Originally posted by AvBaeyer  | However, acylations to give ketones (acetic anhydride + iodine) were shown to be possible if the aromatic substrate is reactive enough. Anisole,
furan, and thiophene are known to give the acyl derivatives. I do not have the references immediately at hand but the work was done in the 1950's.
AvB |
I've actually seen this one before. I found it at JACS vol. 68, 2639 (1946). I've yet to do anything iodine-catalyzed of this nature, I'm glad someone here has tried it.
[Edited on 16-7-2016 by CRUSTY]
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
