CuReUS - 15-9-2014 at 06:55
hi all
i was wondering if you could help me come up with a decent synthetic route to get hexamethylethane(2,2,3,3 tetramethylbutane)
this is what i came up with
1.take para xylene(1,4 dimethylbenzene) and perform birch reduction to get 3,6 Dimethyl-1,4 cyclohexadiene
2.do free radicle bromination to get 3,6 dibromo-3,6 Dimethyl cyclohexadiene
3.perform intramolecular wurtz reaction to get the bicyclo compound 1,4-Dimethylbicyclo(2.2.0)hexa-2,5-diene
4.do ozonolysis to break the two double bonds to get 1,2 dimethyl-1,1,2,2-ethanetetracarbaldehyde
5.finally do wolff kishner reduction of the carbonyl groups to methyl groups to get hexamethylethane
bbartlog - 15-9-2014 at 09:39
I would look at the feasibility of a symmetrical cross-coupling reaction of tert-butyl halides (something akin to a Wurtz coupling). For example, see
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S... From my brief skimming of this document their yield for cross-coupling of
tert-butyl iodide was only 10%, but I'm guessing this would still be higher yielding and certainly easier than the somewhat extravagant route you
propose. Anyway, a more thorough search on symmetrical cross-coupling reactions for alkyl halides might turn up some more promising i.e.
higher-yielding way of performing the reaction.