par De Clercq, M.;Martin, Richard 
Référence Bulletin des Sociétés chimiques belges, 64, 7-8, page (367-385)
Publication Publié, 1955
Référence Bulletin des Sociétés chimiques belges, 64, 7-8, page (367-385)
Publication Publié, 1955
Article révisé par les pairs
| Résumé : | Several new polymethylpyrenes have been synthesised in order to test them for possible carcinogenic activity. Formylation of 3‐methylpyrene (german nomenclature) gives a complex mixture of aldehydes from which 3‐methyl‐5‐formylpyrene (m.p.: 102‐103°) has been isolated. It has been shown that 3‐methyl‐10‐formylpyrene is also present in the reaction mixture. Reduction (Huang‐Minlon) of the formyl derivatives affords 3,5‐dimethylpyrene (m.p.: 98‐99°) and 3,10‐dimethylpyrene (m.p.: 129‐130°) respectively. Treatment of 3,8‐dibromopyrene with butyl‐lithium followed by methyl sulfate gives the isomeric 3,8‐dimethylpyrene (m.p.: 165‐166°). 3,5‐Dimethyl‐8‐formylpyrene (m.p.: 171‐172°), 3,8‐dimethyl‐5‐formylpyrene (m.p.: 187°) and 3,10‐dimethyl‐5‐formylpyrene (m.p.: 175‐176°) are obtained by formylation of the above corresponding dimethylpyrenes. These isomeric aldehydes all give 3,5,8‐trimethylpyrene (m.p.: 178‐179°) on reduction. Further formylation and reduction affords 3,5,8‐trimethyl‐10‐formylpyrene (m.p.: 275‐276°) and 3,5,8,10‐tetramethylpyrene (m.p.: 269‐270°). Formylation of 4‐methylpyrene (new preparation given) followed by reduction gives a dimethylpyrene (m.p.: 62°) different from 3,4‐dimethylpyrene (m.p.: 104‐105°) and which, therefore, probably is the 4,8‐dimethylpyrene. The intermediate 4‐methyl‐8‐formylpyrene (m.p.: 93‐94°) was isolated. U. V. Spectra of the new polymethylpyrenes are given. Copyright © 1955 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim |
