Selective Synthesis of Novel Cyclic Phenylazomethine Trimers
- 10 August 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (18) , 5680-5684
- https://doi.org/10.1021/jo000509c
Abstract
Novel cyclic phenylazomethine trimers (CPAs) were synthesized in a one-step dehydration of the 4-aminobenzophenone derivatives in the presence of TiCl4 or p-toluenesulfonic acid (PTS). The CPAs were isolated in over 90% yield under nondilute conditions. When using TiCl4 as the dehydration agent, the induction of bulky substituents at the α-position of the substrate enhanced the yields of the CPAs. On the other hand, PTS served as an effective catalyst for the synthesis of the phenyl-substituted CPA. This different reactivity between TiCl4 and PTS depends on the dehydration mechanism being dominated by a kinetic process or thermodynamic one. The obtained CPAs were confirmed by NMR, UV−vis spectra, and MM2 calculation to have only a Z conformation and a nonconjugated structure compared to the linear oligophenylazomethines (OPAs) and the aniline-capped OPAs (OPA's).Keywords
This publication has 25 references indexed in Scilit:
- Selective and Efficient Synthesis of Cyclic Hexakis(thio-1,4-phenylene) through Oxidative Polymerization of Diphenyl DisulfideMacromolecules, 1997
- Synthesis, Structure, and Ring-Opening Polymerization of Macrocyclic Aromatic Esters: A New Route to High-Performance PolyarylatesMacromolecules, 1997
- A macrocyclic aromatic thioether ketone: synthesis, structure and anionic ring-opening polymerisationJournal of Materials Chemistry, 1997
- Macrocyclic Arylene Ether Ether Sulfide Oligomers: New Intermediates for the Synthesis of High-Performance Poly(arylene ether ether sulfide)sMacromolecules, 1997
- X-ray crystallographic structure of cyclic tetramer ester based on bisphenol-A and o-phthaloyldichloridePolymer, 1996
- Synthesis and Novel Free-Radical Ring-Opening Polymerization of Macrocyclic Oligomers Containing an Aromatic Sulfide LinkageMacromolecules, 1995
- Convenient Synthesis and Facile Polymerization of Cyclic Aryl Ether Ketones Containing the 1,2-Dibenzoylbenzene MoietyMacromolecules, 1995
- Macrocyclic aramides (2n-aza[2n]paracyclophane-2n-ones): new intermediates for the synthesis of p-aramidsMacromolecules, 1993
- Synthesis and characterization of poly(2-methoxy-5-nitro-1,4-phenylenevinylene) and poly(1,4-phenylenevinylene-co-2-methoxy-5-nitro-1,4-phenylenevinylenes)Macromolecules, 1993
- Synthesis and electrical conductivities of poly(2,3,5,6-tetramethoxy-1,4-phenylenevinylene) and a series of poly(1,4-phenylenevinylene-co-2,3,5,6-tetramethoxy-1,4-phenylenevinylenes)Macromolecules, 1993