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Topic: Mechanism in dodecahedrane synthesis?  (Read 6653 times)

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Offline puppy8800

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Mechanism in dodecahedrane synthesis?
« on: July 07, 2008, 10:19:02 PM »
Hello, could anyone explain the mechanisms of these two steps (see attachment) in dodecahedrane synthesis?
The article on Wikipedia explains no more than this and I am confused..
Thanks in advance.
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Offline Mitch

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Re: Mechanism
« Reply #1 on: July 07, 2008, 10:37:24 PM »
I don't see some of those steps in the original paper?

Total synthesis of dodecahedrane
Leo A. Paquette, Robert J. Ternansky, Douglas W. Balogh, and Gary Kentgen
J. Am. Chem. Soc.; 1983; 105(16) pp 5446 - 5450; DOI: 10.1021/ja00354a043

Link: http://dx.doi.org/10.1021%2Fja00354a043
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Offline puppy8800

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Re: Mechanism in dodecahedrane synthesis?
« Reply #2 on: July 07, 2008, 11:19:10 PM »
Might be another route. The diagram was redrawn from the image on wikipedia (http://en.wikipedia.org/wiki/Image:DodecahedraneSynthesisStepIII.png).
Original synthesis of dodecahedrane used diphenylcyclopropylsulfonium ylide and formed a four-member intermediate, followed by H2O2 oxidation. The latter step is the same.
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Offline Mitch

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Re: Mechanism in dodecahedrane synthesis?
« Reply #3 on: July 07, 2008, 11:44:32 PM »
I don't see how AlCl3 is involved in the Freidel-Crafts step, where is the cation formed?
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