Arylbis(9-anthryl)methyl cations: Highly crowded, near infrared light absorbing hydrocarbon cations

Angewandte Chemie - International Edition

Volumn 43, Issue 37, 2004, Pages 4947-4950

  Nishimae, Yuichi ^a   Kurata, Hiroyuki ^a   Oda, Masaji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Cations; Cycloaddition; Nucleophilic addition; Photochemistry; Steric hindrance

Indexed keywords

ABSORPTION; BENZENE; HYDROCARBONS; ORGANIC ACIDS; POSITIVE IONS;

CYCLIZATION; NEAR INFRARED REGIONS;

METHANOL;

4 METHYLBENZOIC ACID; ANISIC ACID; ANTHRACENE; ANTHRACENE DERIVATIVE; BENZENE DERIVATIVE; BIS(9 ANTHRYL)METHYL ION; CATION; HYDROCARBON; METHYL GROUP; NAPHTHYL GROUP; PHENYL GROUP; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; INFRARED RADIATION; MOLECULAR STABILITY; NAZAROV CYCLIZATION; RADIATION ABSORPTION; SYNTHESIS;

EID: 4744363955     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460480     Document Type: Article

References (20)

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12. Compound 4 has been prepared by Friedel-Crafts acylation of anthracene with 9-anthracenecarbonyl chloride in rather poor yield (21%).[6b] We found that the oxidation of bis(9-anthryl)-methyl alcohol-readily obtainable by the reaction of 9-anthral-dehyde with 9-anthryllithium-with 2,3-dichloro-5,6- dicyano-1,4-quinonediimine (DDQ) in THF at room temperature affords 4 in 95% yield. Oxidation of the alcohol with pyridinium chlorochromate (PCC) resulted mostly in fragmentation to give 9-anthraldehyde and other compounds.
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18. Measured in our laboratory under similar conditions for 3a-e.
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