1. Amines Related to 2,5-Dimethoxyphenethylamine, Richard Baltzly, Johannes S. Buck, ,J. Am. Chem. Soc., 1940, 62 (1), pp 164–167, DOI: 10.1021/ja01858a047.
2. New Method for Direct Conversion of Amides to Amines. ,G. Marc Loudon et. al. J. Org. Chem., Vol. 44, No. 10, 1979, DOI: 0022-3263/79/1944-1746$01.00/0.
3. A Re-examination of Limitations of the Hofmann Reaction. Ernest Magnien, Richard Baltzly, J. Org. Chem., 1958, 23 (12), pp 2029–2032, DOI: 10.1021/jo01106a630.
4. Development of the Hofmann Rearrangement of Nr-Tosylasparagine through Calorimetric and NMR Analysis. Joseph S. Amato et. al., J. Org. Chem. 1998, 63, 9533-9534, 10.1021/jo980799l CCC: $15.00.
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Could anyone post these references up please? Especially number 2..
I have read that dioxane can be a good co-solvent, problem is its not very accessible to myself.
Redeemed, its not hard to get SOMETHING out of this reaction, if you follow the steps in my first post, you will get there.
Im thinking for my next run I will dissolve the amide in minimum amount EtOH and drip this into the basic NaOCl solution. What does everyone think?
I have tried 2 different bleach sources for those wondering, one was the 12% pool stuff and the other was 4.5% industrial cleaner sold at the local hardware store. They gave identical results.
Given that so much amide is coming out at the end of the reaction I assume the major problem here is generating the chloroamide.