Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/95113
Title: Synthesis of 2-Aryl-10b,10c-dimethyl-10b,10c-dihydropyrenes and a Study of Their Conjugation Behavior: Linear Relationship between the Degree of Conjugation and the Electronic Nature of Substituents
Authors: Lai, Y.-H. 
Jiang, J.
Issue Date: 1997
Source: Lai, Y.-H.,Jiang, J. (1997). Synthesis of 2-Aryl-10b,10c-dimethyl-10b,10c-dihydropyrenes and a Study of Their Conjugation Behavior: Linear Relationship between the Degree of Conjugation and the Electronic Nature of Substituents. Journal of Organic Chemistry 62 (13) : 4412-4417. ScholarBank@NUS Repository.
Abstract: A new Gomberg-Bachmann reaction between 10b,10c-dimethyl-10b,10c-dihydropyrene (3) and an arenediazonium salt under acidic conditions afforded a mixture of mono- and diarylated derivatives of 3. The major product was 2-aryl-10b,10c-dimethyl-10bc,10c-dihydropyrene 6. The desired products were obtained only from diazonium salts prepared from anilines with at least one strongly electron-withdrawing substituent. The combined conjugation and electronic effects of the arene substituent on the diatropicity of the dihydropyrene moiety in the monoarylated product is insignificant. The conjugation effect in 6 is, however, readily observed by the color appearance of 6 in the solid state and the significant red shift in the absorption bands between 300 and 520 nm in its electronic spectrum. A linear relationship was in fact obtained when the degree of conjugation (ρ band λmax values) is correlated with the electronic nature (σ+ values) of the corresponding substituents.
Source Title: Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/95113
ISSN: 00223263
Appears in Collections:Staff Publications

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