The syntheses of I-methyl-, 1,l-dimethyl-, cis(?)-l,2-dimethyl-, 1,1,2-trimethyl-, and 1,1,2,2-tetramethylacenaphthene have been accomplished by standard reactions from the two compounds l-acenaphthenone and Zmethyl-1-acenaphthenone. These two ketones were in turn obtained from l-naphthaleneacetic acid.
The reaction of metallic lithium and potassium with indene and floorene in reflusing 1,2-di~nethosyethane (DivIE) yields reduction products of indene and fluorene, 1-metalated indene, and 9-metalated fluorene, and as well is accompanied by the production of some hydrogen gas due to the acidic rnethylene group. The amount of hydrogen is small for fluorene b u t quite substantial for indene.Metalation of indene, 1-methylindene, and 3-methylindene in reflusing DME, followed by methylation of these metalated indenes a t OD, gave a misture consisting of starting material, the corresponding indan, nio~lo~iiethylindene, din~ethylindene, and in some cases trimethylindene. Two competing reaction mechanisms resulting in the formati011 of the metalated indenes are suggested and possible routes for the foriliation of the di-and tri-methylindenes are examined.
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