Some unusual hydrocarbons derived from naphthalene

✍ Scribed by P.R. Houlton; W. Kemp

• Book ID: 104214127
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 203 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)72870-x

✦ Synopsis

Reaently (1) we reported the formation of an unusual ring system in a synthetic sequence starting from (1,8-naphthylenedimethylene)bis-(triphenylphosphoni~ bromide), I. Further reactions in this series have been examined and shown to lead to unexpected products. Other synthetic routes to similar hydrocarbons are also discussed. Clearly deoarboxylation has oaused loss of carbon, subsequent P-position leading to the naphthophenalone XV. The hydrocarbons by repeated chromatography on alumina are XVI and XVII. No.38 arylation in the isolated from the reduction Compound XVI, 7,8-(1',2'-naphtho)phenalene: !?$d overall from the mixed ketones; m.p. (from benzene/petrol, 40-60') 210'. Calculated for C2,H,4, C, 94.74; H, 5.26. Found, C, 94.12; H, 5.0% ~_(EtOH), 216 v (loge 4,00), 261 m)l (4.46), 280 w (k17), 289 sq.~ (3.85), 333 w (3.77). %ar 1.9-2.7, ~~~5.6. Compound XVII, 7,8-b*,2*-(1',2',31,4fi-tetrahydronephtho) 1 phenalene: 2$ overall from the mixed ketones; m.p. (from benzene) 155'.