Pumukli
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Hofmann rearrangement question
Hello,
For a long time I have a question about one particular aspect of doing the above mentioned rearrangement. Here it comes:
Would it be possible to use straight, store bought NaOCl solution (bleach) instead of freshly made NaOBr soln in this reaction?
(After titrating the hypochlorite content of the bleach say with KI/starch/Na2S2O3 or something appropriate redox titration.)?
Hints are welcome! :-)
[Edited on 9-3-2015 by Pumukli]
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morganbw
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It may/should be possible.
There seems to be some literature pointing this way. (not sure on the OTC part, but try it.)
This link does not point to the full article but might help in your research.
An efficient modification of the Hofmann rearrangement: synthesis of methyl carbamates
Wiki also mentions NaOCl as a variant.
Perhaps others will step in to fill in the blanks.
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gdflp
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Yes it is possible, I have done it before and it works well. Here is an example of a Hofmann Rearrangement using store bought bleach, it's a J. Chem
Ed article, it's just on another site so that you can read the whole article. http://works.bepress.com/cgi/viewcontent.cgi?article=1021&am...
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