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The Hive => Serious Chemistry => Topic started by: Rhodium on August 28, 2001, 08:18:00 AM

Title: p-benzoquinone addition mechanism?
Post by: Rhodium on August 28, 2001, 08:18:00 AM

p-Benzoquinone reacts with trialkylboranes to give 2,5-dihydroxyalkylbenzenes, with sodium thiosulfate to give 2,5-dihydroxyphenylthiosulfate etc.

What is the mechanism behind this? What other stuff can generally be added to p-benzoquinone? I would very much like to have some kind of review article on addition to benzoquinone, besides the obvious diels-alder pericyclic addition. Anyone here who could help me with a reference of some sort?

Title: Re: p-benzoquinone addition mechanism?
Post by: Natrix on September 11, 2001, 01:58:00 AM

I'm not sure if this:

http://www.geocities.com/i998877/ (http://www.geocities.com/i998877/)

is what you are looking for. I hope you can read it.

Title: Re: p-benzoquinone addition mechanism?
Post by: Rhodium on September 11, 2001, 06:13:00 AM

Thank you, exactly what I'm looking for. What reference is it taken from, Chemishe Berichte?

I don't want to be picky when I got all this from you, but the pages 608, 616 and 620 is missing, and there are doublets of 622, 623 and 625 in their places...

Title: Re: p-benzoquinone addition mechanism?
Post by: Natrix on September 12, 2001, 05:16:00 AM

The documents are from Houben-Weyl: Methoden der organischen Chemie (

http://www.indiana.edu/~cheminfo/h-wguide.html (http://www.indiana.edu/~cheminfo/h-wguide.html)

). You might find it in your library. I'll scan the missing pages and put them on the web.

Title: Re: p-benzoquinone addition mechanism?
Post by: Natrix on September 14, 2001, 03:51:00 AM

should be o.k. now:

http://www.geocities.com/hon5rrnfd/ (http://www.geocities.com/hon5rrnfd/)

and there is other stuff at:

http://www.geocities.com/x6534fzz/ (http://www.geocities.com/x6534fzz/)