I'm going to prepare a polyamine from polyacrylamide or polyacrylonitrile. I want to know if the Clemmensen reduction is a good way to convert the nitrile or amide groups into the amines? Does anyone have any good references?
In my opinion a Clemensen reduction may be too harsh.....Ther are some different methods for reducing nitriles to amines....ex. LAH/diethyl ether; AlH3/THF or NaBH4/BF3 Et2O. In the last method NaBH4 generates B2H6 which is reducing agent. Amides can be reduced to amines via LAH/Et2O or B2H6/THF. Much more methods you can find also in an excelent book by R.C.Larock: COMPREHENSIVE ORGANIC TRANSFORMATIONS A Guide to Functional Group Preparations Second Edition By Richard C. Larock WILEY-VCH New York • Chichester • Weinheim 1999. Hundreds reaction and more with literature references....
Sincerely,
Andrzej Danel
See this http://www.organic-chemistry.org/synthesis/N1H/reductionsnitriles.shtm, http://www.commonorganicchemistry.com/Rxn_Pages/Nitrile_to_Amine/Nitrile_to_Amine_Index.htm, and this http://www.dow.com/sbh/pdfs/venpure_amide.pdf.
I agree with Danel, You can also use NaBH4/I2 system for in situ generation of Borane.
Ref: Tetrahedron Vol. 48, No. 22, PP. 4623-4628.1992
Simply use Sn/Hcl which is better than Fe/Hcl as Fe/HCl as previous one has an edge in improving the yield
Thanks for your suggestions. Dear Arvind, Could you please suggest any good references that used of Sn/Hcl or Fe/HCl for nitril or amide reduction?
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