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- Title
Transamidation reactions. Part 11. N-substituted 3-aminopropanenitriles and 2-aminoacetonitriles as Schiff-base equivalents.
- Authors
Askitoǧlu, Elefteria; Guggisberg, Armin; Hesse, Manfred
- Abstract
In presence of a strong base, the 13-membered cyclic compound 3 yielded, by loss of acetonitrile or its equivalent, the bicyclic product 5 instead of the 17-membered compound 4 as expected (Scheme 2). Investigation of model compounds (Scheme 4) and of model reactions ( Schemes 5 and 6) led to the conclusion that the reaction proceeds via an intermediate formaldehyde imine; a Schiff base, e.g. 3b (Scheme 5), which reacts intra- and intermolecularly with a nucleophile to form a Mannich-type product. It seems to be a general principle that N-substituted 3-aminopropanenitrile and 2-aminoacetonitrile derivatives behave in the presence of a strong base as Schiff -base equivalents ( Schemes 5 and 6).
- Publication
Helvetica Chimica Acta, 1985, Vol 68, Issue 3, p750
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19850680325