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ADDP

[1,1'-(Azodicarbonyl)dipiperidine]


Other Names:

1,1'-Azobis(N,N-pentamethyleneformamide)

Azodicarboxylic acid dipiperidide

ADD




General Information:


Structure:



CAS Number: 10465-81-3

Molecular Weight: 252.31 g/mol

Melting Point: 134-136 C


1,1-(Azodicarbonyl)dipiperidine (ADDP) is typically used as a reagent in Mitsunobu reactions. ADDP is an Azo-type reagent that enables Mitsunobu reactions with certain substrates that react poorly or fail with DEAD-TPP systems. DEAD-TPP Mitsunobu reactions generally only work well with substrates that have a pKa < 11. Azo-type reagents are more easily protonated by less acidic substrates, therefore should allow more successful reactions when substrates have a pKa near the limits of the DEAD-TPP system's abilities, which as mentioned before is at pKa ~11.


Azo-type reagents are poorer Michael acceptors than DEAD, therefore they are generally paired with more nucleophilic phosphine reagents than TPP, such as tributylphosphine or trioctylphosphine.




Common Uses:


Reagent in Mitsunobu reactions



Procedure excerpt:

. . . was added ADDP (0.192 g, 0.761 mmol) and the mixture was again sparged with N2 and stirred an additional 10 min. Trioctylphosphine (0.40 mL, 0.81 mmol) was added . . .

[full procedure]




References:


1) Patent Reference: WO2016014463, page 168, (6.7 MB)

2) www.sigmaaldrich.com: 1,1’-(Azodicarbonyl)dipiperidine (link)

3) www.alfa.com: H27719 1,1’-(Azodicarbonyl)dipiperidine, 97% (link)

4) Tsunoda, Tetsuto; Kaku, Hiroto; Ito, Sho; New Mitsunobu Reagents (TCI Mail) (link)