Article
Synthesis and X-ray structure of a fluorinated 1,1-dialkoxy-3-iminoisoindoline acetal, an elusive phthalocyanine precursor
Tetrahedron
(2018)
Abstract
The synthesis of a fluoroalkylated 1,1-dimethoxy-3-iminoisoindoline acetal, the first representative of the halogenated 3-imino-amino-1-acetal class is reported. In contrast to the protio compound, fluoroalkyl groups make the presence of a base unnecessary for its synthesis while stabilizing the amino tautomer as revealed by an X-ray structural analysis - the first atomic-level structural characterization of the 1,1-alkoxy-3-amino(imino) isoindoline scaffold. Dimers present in solid-state are H-bonded and define a motif similar to the stabilizing, reverse wobble one encountered in adenine-cytosine pairs of tRNA. The fluoro acetal forms easily both metallo- and metal-free phthalocyanines, supporting the proposal that acetals might be phthalocyanine intermediates.
Keywords
- Acetal,
- Perfluoroalkyl,
- Tautomers,
- X-ray structure
Disciplines
Publication Date
July 5, 2018
Citation Information
Sergiu M. Gorun, Erik N. Carrion and Angela T. Dang. "Synthesis and X-ray structure of a fluorinated 1,1-dialkoxy-3-iminoisoindoline acetal, an elusive phthalocyanine precursor" Tetrahedron Vol. 74 Iss. 27 (2018) p. 3697 - 3700 Available at: http://works.bepress.com/sergiu_gorun/12/