Tautomerization in naphthalenediimines: a keto-enamine Schiff base macrocycle.
[reaction: see text] A new [3 + 3] Schiff base macrocycle incorporating naphthalene groups has been prepared. By examination of its properties, X-ray crystallography of model compounds, and calculations, it has been determined that the macrocycle exists predominantly as the keto-enamine tautomer. This unexpected tautomerization presents an unusual hexaketo interior in the macrocycle.
Gallant
Amanda J
AJ
Department of Chemistry, University of British Columbia, Vancouver, Canada.
Yun
Michael
M
Sauer
Marc
M
Yeung
Charles S
CS
MacLachlan
Mark J
MJ