Acidity of Hydrocarbons. XLI. Kinetic acidities of bridgehead hydrogens in benzotriptycene and ethenoanthracene towards cesium cyclohexylamide

✍ Scribed by A. Streitwieser Jr.; M.J. Maskornick; G.R. Ziegler

• Book ID: 104248229
• Publisher: Elsevier Science
• Year: 1971
• Tongue: French
• Weight: 193 KB
• Volume: 12
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)97326-5

✦ Synopsis

We have shown recently (1) that the kinetic acidity of the bridgehead position of triptycene, I, can be quantitatively accounted for on the basis of the s-character in the C-H bond as measured by J13C_H, and by the inductive field effect of the aryl carbons as measured by Cl/r. The success of the Cl/r field effect function prompted a further test by extension to two derivatives of I obtained by adding and removing a benzene ring, respectively: benzo[bltriptycene, II, and 9,10-dihydro-9,10_ethenoanthracene, III.