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Synthèses dans le domaine des hydrocarbures cancérigènes XIII 3,4‐diméthyl‐et 2,3,4‐triméthylpyrènes

par Martin, Richard ;Senders, J.
Référence Bulletin des Sociétés chimiques belges, 64, 5-6, page (221-234)
Publication Publié, 1955

Article révisé par les pairs

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Résumé :

The syntheses of 3,4‐dimethyl‐and 2,3,4‐trimethylpyrenes are described. These new alkyl derivatives of pyrene have both been obtained from 2‐oxo‐3,4‐dimethyl‐1,2,8,9,10,11‐hexahydropyrene (VII). An improved method of preparation of this ketone, involving the following steps, has been worked out: reduction of 4‐oxo‐6‐7‐dimethyl‐1,2,3,4‐tetrahydrophenanthrene (V) with LiAlH4; treatment of the resulting alcohol with HCl, malonic ester condensation, hydrolysis, decarboxylation and finally cyclisation with anhydrous HF. Reduction of the tetracyclic ketone (VII) with LiAlH4 followed by catalytic dehydration and dehydrogenation with Pd on charcoal, affords the expected 3,4‐dimethylpyrene (IV) (m. p.: 103‐104°). Treatment of VII with CH3MgI, followed by dehydration and dehydrogenation (Pd on charcoal), gives a poor yield of 2,3,4‐trimethylpyrene (IX) (m. p.: 123‐124°). The U. V. spectra of these hydrocarbons were determined. Copyright © 1955 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim