ADDP

CAS 10465-81-3, Cat. No EN300-346030

Reagent for Mitsunobu reaction, selective oxidation of a variety of alcohols

1,1'-(Azodicarbonyl)dipiperidine or ADDP is a versatile reagent, but typically used as a reagent in Mitsunobu reactions. It’s stable golden-yellow crystals, soluble ethanol, ether, THF, and slightly soluble in methanol. ADDP is an Azo-type reagent that enables Mitsunobu reactions with certain substrates that react poorly or fail with DEAD-TPP systems, due to a low acidity of substrates. But except Mitsunobu reaction, ADDP can oxidate a wide variety of primary and secondary alcohols, after alcohols are converted into their bromomagnesium salts. This method has been employed to oxidize a wide range of alcohols incorporating functional groups such as alkenes, epoxides, amines, sulfides, allylstannanes, and allenylstannanes. Acylstannanes can also be prepared by the oxidation of the lithium salt of 1-stannyl alcohols.

Synonyms: 1,1′-(1,2-Diazenediyl)bis[1-(1-piperidinyl)methanone]; Diimide, bis(piperidinocarbonyl); Piperidine, 1,1′-(azodicarbonyl)bis-; 1,1′-(Azodicarbonyl)bis[piperidine]; 1,1′-(Azodicarbonyl)dipiperidide; 1,1′-(azodicarbonyl)dipiperidine; 1,1′-Azobis(N,N-pentamethyleneformamide); Azodicarbonyldipiperidine

Selected publication

1. 1,1′-(Azodicarbonyl)Dipiperidine.

Narasaka K.; Kusama H. Encyclopedia of Reagents for Organic Synthesis 2001. DOI: 10.1002/047084289X.ra122