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- Title
A Short-Step Synthesis of 1,6-Methano[10]annulene-3,4-dicarboximides and Their Benzene-, Naphthalene-, and Thiophene-Annulated Compounds.
- Authors
Oda, Mitsunori; Nakamura, Tomomi; Neha, Miyako; Miyawaki, Daisuke; Ohta, Akira; Kuroda, Shigeyasu; Miyatake, Ryuta
- Abstract
Triphenylphosphorane reagents 8 react with 1,3,5-cycloheptatriene-1,6-dicarbaldehyde ( 2) under acidic as well as basic conditions to produce 1,6-methano[10]annulene-3,4-dicarboximides 1 in moderate -to- good yields. The reagents 8 react with 3,4-arene-annulated 1,3,5-cycloheptatriene-1,6-dicarbaldehydes 9, 10, and 11 to afford only the Wittig condensation products under acidic conditions but produce the arene-annulated annulenedicarboximides under basic conditions. The structures of some of the dicarboximides and the intermediate Wittig condensation products were determined by X-ray structural analysis. The emission properties of the dicarboximides were also studied.
- Subjects
IMIDES; ANNULENES; ANNULATION; DICARBOXIMIDES; CHEMICAL reactions; AROMATIC compounds
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 27, p5976
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201402776