Lithiation in α‐Position to the N‐Atom of Triphenylacetamides from Cyclic Secondary Amines. Rearrangements of Metalated Triphenylacetamides by 1,3‐Shift of Carbamoyl Groups
The reagents 2 ‐ generally available by lithiation of the triphenylacetamides 1 ‐ react with non‐enolizable carbonyl compounds and benzyl halide (s. Tables 1 and 2, and products 3). The limits of thermal stability of metalated triphenylacetamides above 0° are caused by a 1,3‐shift of the carbamoyl group into the o‐position of one of the benzene rings (s. 2b → 4 and 8a → 10). The barriers to rotation around the amide bonds of four triphenylacetamides are ca. 16 kcal/mol (s. 1b–e in Table 1).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.