Chemical Forums
1 Hour
1 Day
1 Week
1 Month
Forever
December 23, 2024, 09:08:53 PM
Forum Rules
: Read This Before Posting
Home
Help
Search
Login
Register
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
Organic Chemistry Forum for Graduate Students and Professionals
Mechanism in dodecahedrane synthesis?
« previous
next »
Print
Pages: [
1
]
Go Down
Topic: Mechanism in dodecahedrane synthesis? (Read 7225 times)
0 Members and 2 Guests are viewing this topic.
puppy8800
Regular Member
Posts: 22
Mole Snacks: +1/-3
Gender:
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.
Logged
Mitch
General Chemist
Administrator
Sr. Member
Posts: 5298
Mole Snacks: +376/-3
Gender:
"I bring you peace." -Mr. Burns
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
Logged
Most Common Suggestions I Make on the Forums.
1. Start by writing a balanced chemical equation.
2. Don't confuse thermodynamic stability with chemical reactivity.
3.
Forum Supports LaTex
puppy8800
Regular Member
Posts: 22
Mole Snacks: +1/-3
Gender:
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 H
2
O
2
oxidation. The latter step is the same.
Logged
Mitch
General Chemist
Administrator
Sr. Member
Posts: 5298
Mole Snacks: +376/-3
Gender:
"I bring you peace." -Mr. Burns
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?
Logged
Most Common Suggestions I Make on the Forums.
1. Start by writing a balanced chemical equation.
2. Don't confuse thermodynamic stability with chemical reactivity.
3.
Forum Supports LaTex
Print
Pages: [
1
]
Go Up
« previous
next »
Sponsored Links
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
Organic Chemistry Forum for Graduate Students and Professionals
Mechanism in dodecahedrane synthesis?