Tautomerization in naphthalenediimines: a keto-enamine Schiff base macrocycle | Health & Environmental Research Online (HERO)

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HERO ID

1468660

Reference Type

Journal Article

Title

Tautomerization in naphthalenediimines: a keto-enamine Schiff base macrocycle

Author(s)

Gallant, AJ; Yun, M; Sauer, M; Yeung, CS; Maclachlan, MJ

Year

2005

Is Peer Reviewed?

Journal

Organic Letters
ISSN: 1523-7060
EISSN: 1523-7052

Volume

Issue

Page Numbers

4827-4830

Language

English

PMID

16235899

DOI

10.1021/ol051511z

Web of Science Id

WOS:000232817700011

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-27644477899&doi=10.1021%2fol051511z&partnerID=40&md5=3f92eec3a626067334698fb8e727f9c6
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Abstract

[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.