par Hebbelynck, Marcel 
;Martin, Richard
Référence Bulletin des Sociétés chimiques belges, 61, 11-12, page (635-650)
Publication Publié, 1952
;Martin, Richard Référence Bulletin des Sociétés chimiques belges, 61, 11-12, page (635-650)
Publication Publié, 1952
Article révisé par les pairs
| Résumé : | 1,2‐di‐(1′‐méthyl‐naphthyl‐2′)ethane (IX) has been prepared, starting from 1‐bromo‐2‐methylnaphthalene, by the following steps: bromination with N‐bromsuccinimide [1‐bromo‐2‐bromomethylnaphthalene (VII)] condensation (Fe) [1,2‐di‐(1′‐bromo‐naphthyl‐2′) ethane (VIII)] and treatment of the dibromo derivative with BuLi and (CH3)2SO4. Attempt cyclodehydrogenation of 1,2‐di(1′‐methyl‐naphthyl‐2′)‐ethane with AlCl3 in CS2 did not give the expected 1,8‐dimethyl‐2,3,6,7‐dibenzphenanthrene (I d). The constitution of the reaction product (m.p.: 173‐174°) has not yet been elucidated. 1,2‐di‐(2′‐methyl‐naphthyl‐1′)ethane (XVI) and 1,2‐di(4′‐methylnaphthyl‐1′)ethane (XVIII) have been obtained from 2‐methyl‐1‐chloromethylnaphthalene and 4‐methyl‐1‐chloromethylnaphthalene respectively. Treatment of 1,2‐di(4′‐methyl‐naphthyl‐1′)ethane (XVIII) with AlCl3 in CS2 afforded 11,14‐dimethylpicene (XIX) in approximately 30% yield. The U.V. spectra of 1,2‐di(1′‐methyl‐naphthyl‐2′)ethane, 1,2‐di(2′‐methyl‐naphthyl‐1′)ethane, 1,2‐di(4′‐methyl‐naphthyl‐1′)ethane and 11,14‐dimethylpicene are given. Copyright © 1952 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim |
