Bridgehead Cations of Tricyclo[5.2.1.04, 10]deca-2,5,8-triene (Triquinacene)

✍ Scribed by Dr. Dieter Bosse; Prof. Dr. Armin de Meijere

• Publisher: John Wiley and Sons
• Year: 1976
• Tongue: English
• Weight: 231 KB
• Volume: 15
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.197605571

✦ Synopsis

imentally determined activation energy for the 1,2 hydride shift on the 2-norbornyl cation is 10 kcal/mol[q.

These relative energy predictions have now been confirmed e~perimentalIy[~l. The calculated flattening of the carbenium ion into an almost planar divinylcarbenium ion is supported by the 'Hand I3C-NMR spectra[4! Calculation with a UHF open-shell version of MINDO/3"] shows the same stability sequence for the radicals (2') and (3'): Radical (2') is about IOSkcal/mol more stable than (3'). The calculated structural data are also listed in Table