
TY  - JOUR
A1  - Acott, B 
A1  - Beckwith, ALJ 
A1  - Hassanali, A 
T1  - Reactions of lead tetraacetate. I. Formation of acylamines from primary carboxamides
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1968
VL  - 21
IS  - 1
SP  - 185
EP  - 195
KW  - 
UR  - https://doi.org/10.1071/CH9680185 
N2  - Pentanamide, when treated with lead tetraacetate in hot benzene, affords a mixture of N-butylacetamide and N,N?-dibutylurea. Examples of similar transformations of a number of primary carboxamides are described. The reaction, which may also be conducted in acetic acid or benzene-acetic acid mixture, is catalysed by pyridine. Cyclohexanecarboxamide, when oxidized by lead tetraacetate in the presence of propionic or benzoic acid, is converted into the appropriate acylcyclohexylamine. The reaction mechanism involves intermediate formation of alkyl isocyanate, possibly via Curtius rearrangement of acylnitrene. 
ER  -

