Lambda
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DEAD
DEAD - (D)i(E)thyl (A)zo(D)icarboxylate
DEAD is actually the acronym for diethyl azodicarboxylate, which is an important reagent in the well-known Mitsunobu reaction which performs a
stereospecific conversion of an alcohol to a primary amine. It's quite a good acronym, as DEAD is an orange liquid that's explosive, shock sensitive,
light sensitive, toxic, a possible carcinogen or mutagen, and an eye, skin and respiratory irritant! A version of (D)i(E)thyl (A)zo(D)i(C)arboxylate
mixed with (A)cid and (T)riphenylphosphine has also been termed DEADCAT.
DEAD:
----------O-------O-----------
C-C-O-C-N=N-C-O-C-C
Remark:
O
C must be seen as C=O
[Edited on 1-1-2007 by Lambda]
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JohnWW
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DEAD: That would be CH3-CH2-O-C(O)-N=N-C(O)-CH2-CH3 . I have seen it listed in a Sigma-Aldrich catalog. The orange color is to be expected from the
conjugated system of O=C-N=N-C=O in it, but it is probably too volatile and dangerous to use as an azo-dye. Do you have any PDF files on the Mitsunobu
alcohol -> primary amine reaction?
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Lambda
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Hi @JohnWW,
Here you have a few PDF-articles and Web-related sources to "Mitsunobu Chemistry". The References given in these articles lead to a much more
resourceful and in depth discussion of the subject. These links are probably not the best to be found on the Net, but I hope you may still find them
useful.
Links (I have renamed the PDF-file titles above the link):
The Mitsunobu Reaction - By Kevin Jantzi (12 April 2001) 8s.pdf
http://www.chem.wisc.edu/areas/organic/studsemin/jantzi/jant...
A Whirlwind Tour of Current Mitsunobu Chemistry - By R. Jason Herr (Albany Molecular Research - Technical Report, Vol. 3, No. 19, 1999) 36s.pdf
http://www.designer-drug.com/pte/12.162.180.114/dcd/pdf/curr...
New Mitsunobu Reagents (TCIMAIL No. 123) 10s.pdf
http://tciamerica.com/contrib/bun/123drE.pdf
Recently Modified Mitsunobu Reactions (Chemical Note No. 104) 4s.pdf
http://www.tciamerica.com/note_e/104chem.pdf
Mitsunobu reaction - HTM
http://www.answers.com/topic/mitsunobu-reaction
Diethyl azodicarboxylate - DEAD - HTM
http://www.answers.com/topic/diethyl-azodicarboxylate
Regards,
Lambda.
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