Ion pairs as intermediates in the rearrangements of the dibenzocycloheptatrienyl-methyl and dibenzocyclooctatrienyl systems

✍ Scribed by Ecaterina Cioränescu; Aurora Bucur; M. Elian; M. Banciu; M. Voicu; C.D. Nenitzescu

• Book ID: 104244417
• Publisher: Elsevier Science
• Year: 1964
• Tongue: French
• Weight: 218 KB
• Volume: 5
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93302-7

✦ Synopsis

By acetolysis of the 1:2.5:6-dibensocyclohepta-1.3.5trienyl-T-methyl tosylate (Ib) in glacial acetic acid the unrearranged acetate Ic was obtained together with a small amount of dibenzocyclooctatetraene (III). On the other hand 1:2.5:6-dibenzocycloocta-1.5.5-triene-T-01 acetate (IIb) was t'ne only product if solvolysis proceeds in the presence of sodium acetate (1). In both cases maximum yields are more than 9%. The proportions of the products corresponding to different concentrations of sodium acetate are given in table I. La O?=H) Ib (R=rne> Ic (IbAa) ILa (I&H) III IIb (IDOCH3)