ADDP

CAS 10465-81-3, Cat. No EN300-346030
Reagent for Mitsunobu reaction, selective oxidation of a variety of alcohols

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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 methanol¹. 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 substrates¹. 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 allenylstannanes¹. 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