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- Title
Lithiierung in α-Stellung zum N-Atom von Triphenylacetamiden aus cyclischen sekundären Aminen. Umlagerung metallierter Triphenylacetamide unter 1,3-Verschiebung der Carbamoylgruppe.
- Authors
Wykypiel, Werner; Lohmann, Jean-Jaques; Seebach, Dieter
- Abstract
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).
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 5, p1337
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640510