Synthesis of a series of novel polycyclic aromatic systems: isomers of benz(a)anthracene containing a cyclopenta-fused ring
The four possible isomers of benz(a)anthracene containing a cyclopenta-fused ring have been synthesized and characterized. These systems are of interest for structure-activity studies in bioactivation because of their predicted high level of activity. Formation of fused five-membered rings by intramolecular cyclodehydration, often difficult to accomplish, was found to be smoothly effected in anhydrous hydrofluoric acid (HF), provided the reactivity index (N/sub t/a) for the appropriate electrophilic addition was favorable. The dihydro polycyclic aromatic alcohols obtained from reduction of the corresponding keto cyclodehydration products were best dehydrated to the desired polycyclic aromatic hydrocarbons (PAH) by activity grade I neutral alumina in refluxing benzene. This dehydration proceeds in high yield without the formation of isomeric or polymeric side products that occurred even under such mild acid catalysis as p-toluenesulfonic acid.
- Research Organization:
- Univ. of North Carolina, Chapel Hill
- OSTI ID:
- 5614713
- Journal Information:
- J. Org. Chem.; (United States), Vol. 48:10
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
POLYCYCLIC AROMATIC HYDROCARBONS
CHEMICAL PREPARATION
STRUCTURAL CHEMICAL ANALYSIS
ALUMINIUM OXIDES
AROMATIZATION
BENZANTHRACENE
BENZENE
CARBOXYLIC ACIDS
DEHYDRATION
EXPERIMENTAL DATA
HYDROFLUORIC ACID
ISOMERS
MASS SPECTRA
MUTAGENS
PUBLIC HEALTH
ALUMINIUM COMPOUNDS
AROMATICS
CHALCOGENIDES
CHEMICAL REACTIONS
CONDENSED AROMATICS
DATA
HYDROCARBONS
HYDROGEN COMPOUNDS
INFORMATION
INORGANIC ACIDS
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
SPECTRA
SYNTHESIS
400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)