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|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. |
|Citation:||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|
|Appears in Collections:||Staff Publications|
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