Dear all,
I have found a synthesis for 1,3,5,7-Tetrakisphenyladamantane starting from 1-Bromoadamantane solved in benzene. However I can not really explain what kind of reaction is happening there. The details of the reaction are :
"1-Bromoadamantane (6.00 g, 27.9 mmol, 1.0 equiv.) was dissolved in benzene (60 mL) under argon atmosphere. t-Butylbromide (6.30 mL, 55.8 mmol, 2 equiv.) and AlCl3 (320 mg, 2.40 mmol, 0.1 equiv.) was added to the suspension which was heated under reflux for 2 h. [...] "
(Taken from http://www.rsc.org/suppdata/c5/cy/c5cy00038f/c5cy00038f1.pdf, Section 2.3.1)
I am so far that I understand it is a (kind of) Friedel -Crafts Arylation, but in that case I dont understand why the reaction can use 1-Bromoadamantane as reactant instead of 1,3,5,7 -Tetrakisbromoadamantane. A second question that I have is: what is the role of t-butylbromide? I have thought that it (together with AlCl3) may be able to rip of the H atoms from 1-Bromoadamantane, which then could attack the benzene molecules. But then I would expect that three equivalents of t-butylbromide would be needed instead of only two.
tert.-butyl bromide works as sludge catalyst:
See attachements:
cr60229a004: Page 11 Equation 22
Adamantane rearangements: Sludge catalyst
Dear Juergen,
thank you for the answer, I have checked cr60229a004: Page 11 Equation 22, and I have a small question: Do I understand it correct that this is the overall reaction that we would have?
Ada + tert-Butyl+ --> Ada+ + tert-butane
Ada+ + tert-butyl-Br --> AdaBr + tert-butyl+
AdaBr + C6H6 ---> Ada-C6H5 + HBr
----------------------------------------------------------------------------------
which gives the overall reaction :
Ada + C6H6 + tert-butyl-Br --->Ada-C6H6 + HBr + b-butane
so is tert-butyl-Br actually consumed? If so, does this still correspond to the definition of a "catalyst"? (In the sense that a catalyst is something that is not consumed during a reaction)
Dear Jürgen,
thank you for the answer, I have checked cr60229a004: Page 11 Equation 22, and I have a small question: Do I understand it correct that this is the overall reaction that we would have?
Ada + tert-Butyl+ --> Ada+ + tert-butane
Ada+ + tert-butyl-Br --> AdaBr + tert-butyl+
AdaBr + C6H6 ---> Ada-C6H5 + HBr
----------------------------------------------------------------------------------
which gives the overall reaction :
Ada + C6H6 + tert-butyl-Br --->Ada-C6H6 + HBr + b-butane
so is tert-butyl-Br actually consumed? If so, does this still correspond to the definition of a "catalyst"? (In the sense that a catalyst is something that is not consumed during a reaction)
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