A novel and convenient synthesis of arylnorbornyl cations

✍ Scribed by N.C. Deno; P. von R. Schleyer; D.C. Kleinfelter

• Book ID: 104234990
• Publisher: Elsevier Science
• Year: 1961
• Tongue: French
• Weight: 116 KB
• Volume: 2
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82660-5

✦ Synopsis

BICYCLOHBPTADIENE (I) reacts with benzene and its derivatives in 9'7% sulfuric acid to form ions, the properties of which resemble those of amonoaryl cations. Furthermore, the ions so formed are identical with those produced by the action of concentrated sulfuric acid upon corresponding 2-aryl (II)l and 1-arylnorbornanols (III and IV).1 Cations from I, II, III, and IV exhib:lted the same ultraviolet spectra and possessed the same thermodynamic stabilities. These ions, formulated as V1I,2 are probably formed from II directly, from III and IV by Wagner -Meerwein rearrangement and from I by alkylation to V and/or VI, followed by protonation and 6,2-hydride shift.3 The cations 1 D.C. Kleinfelter, Ph.D. Thesis, Princeton University, l%O. For the synthesis of the arylnorbornanols (II-IV) see D.C. Kleinfelter and P. von R. Schleyer, J.Ora.Chem. &, In press (1961). 2 N.C. Deno, to be published. ' L. Ruzicka in Perspectives in Oraanic Chemistry (Edited by A. Todd) p. 265. Interscience, New York (19%).