Literature DB >> 16235899

Tautomerization in naphthalenediimines: a keto-enamine Schiff base macrocycle.

Amanda J Gallant1, Michael Yun, Marc Sauer, Charles S Yeung, Mark J MacLachlan.   

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.

Entities:  

Year:  2005        PMID： 16235899     DOI： 10.1021/ol051511z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  2 in total

1.  Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides.

Authors:  Perumal Prabhakaran; Perumal Rajakumar
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

2.  Intramolecular Hydrogen Bonds in Normal and Sterically Compressed o-Hydroxy Aromatic Aldehydes. Isotope Effects on Chemical Shifts and Hydrogen Bond Strength.

Authors:  Poul Erik Hansen; Fadhil S Kamounah; Bahjat A Saeed; Mark J MacLachlan; Jens Spanget-Larsen
Journal:  Molecules       Date:  2019-12-11       Impact factor: 4.411
  2 in total

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