ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680325