Reaction of lead tetra-acetate with primary amides. Formation of alkyl carbamates.

✍ Scribed by B. Acott; A.L.J. Beckwith; A. Hassanali; J.W. Redmond

• Book ID: 104250091
• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 241 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99611-x

✦ Synopsis

In a previous communication' we described the formation of l+acetylamines and g,N'-dialkylureas by interaction of primary amides and lead tetra-acetate in benzene or preferably in acetic acid. Evidence was presented in support of the hypothesis that the reaction proceeds initially to the appropriate isocyanate (III) from which the final products, (IV) and (V), were formed by reaction with acetic acid. It was also suggested that the rearrangement (I + III) involves the intermediacy of an acylnitrene (II). Independently, the reaction of lead tetra-acetate with primary amides and t-butanol in the presence n of trietbylamine was studied by Baumgarten and StaklisL who showed that t-butyl oarbamates (VI, Al-t-Bu) are produced under these conditions.

These authors confirmed the initial formation of the isocyanate and they further suggested that the reaction proceeds via a nitrene intermediate.